Substituted isoxazoline or enone oxime compound, and  pest control agent

ABSTRACT

Disclosed is a novel pest control agent, in particular a pesticide or a miticide. Specifically disclosed are a substituted isoxazoline compound or a substituted enone oxime compound represented by the general formula (1) below or the general formula (2) below, and a pest control agent containing any of them. (In the formulae, the symbols are as defined in the description.)

TECHNICAL FIELD

The present invention relates to a novel substituted isoxazoline compound or substituted enone oxime compound and salts thereof, and a pest control agent containing the compounds as active ingredients. The pest control agent in the present invention means insect pest control agents aimed at harmful arthropods in the agriculture and horticulture field or in the livestock/sanitation field (internal or external parasites of mammals or birds as domestic animals or pet animals and sanitary insects and discomfort insects for domestic use and business use). In addition, the agricultural chemicals in the present invention mean insecticides and miticides, nematicides, herbicides, bactericides and the like in the agricultural and horticultural field.

BACKGROUND ART

Conventionally, with respect to substituted isoxazoline compounds, for example, a 5-haloalkyl-5-Substituted aryl-3-Substituted aryl-4,5-dihydroisoxazole compound is known to exhibit pest control activity, particularly insecticidal and miticidal activity (see Patent Documents 1 to 5). However, nothing is disclosed with respect to a 4-Substituted-5-haloalkyl-5-Substituted aryl-3-Substituted aryl-4,5-dihydroisoxazole compound according to the present invention. In addition, with respect to a 3,5-bis substituted phenyl-4-Substituted-5-Substituted-4,5-dihydroisoxazole derivative, known is the synthesis of 5-alkoxycarbonyl-3,5-bis substituted phenyl-4-(substituted phenyl)-4,5-dihydroisoxazole derivative (for example, see Non-patent Document 1), 4-Substituted alkylidene-3-Substituted phenyl-5,5-bis phenyl-4,5-dihydroisoxazole derivative (for example, see Non-patent Document 2), and the like. However, nothing is disclosed with respect to a 4-substituted-5-haloalkyl-5-Substituted aryl-3-Substituted aryl-4,5-dihydroisoxazole compound according to the present invention.

[Patent Document 1]

International Publication No. WO 2005/085216 pamphlet

[Patent Document 2]

International Publication No. WO 2007/026965 pamphlet

[Patent Document 3]

International Publication No. WO 2007/105814 pamphlet

[Patent Document 4]

Japanese Patent Application Publication No. JP-A-2007-016017

[Patent Document 5]

Japanese Patent Application Publication No. JP-A-2007-106756 [Non-patent Document 1]

Heterocycles, vol. 71, p. 289 (2007)

[Non-patent Document 2]

Chemisch Berichte, vol. 119, p. 563 (1986)

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention

The development of pest control agents for the purpose of controlling various pests such as agricultural and horticultural pests, forest pests or sanitary pests has been progressed and until today, various agents have been practically applied.

However, due to the use of such agents for a long period, recently, pests have acquired drug resistance and there has been increased the number of situations in which the control with related art insecticides and bactericides which have been used becomes difficult. In addition, a part of the related art pest control agents has high toxicity or some of them remain in the environment for a long period to disturb the ecosystem, which is becoming a significant problem. Under such a situation, the development of a novel pest control agent having not only high pest control activity, but also low toxicity and a low residual property is constantly expected.

Means for Solving the Problems

As a result of assiduous research intended to overcome these disadvantages, the present inventors have found that a novel substituted isoxazoline compound and substituted enone oxime compound represented by the following General Formula (1) to General Formula (4) according to the present invention exhibit excellent pest control activity, particularly excellent insecticidal and miticidal activity and are extremely useful compounds having substantially no adverse effect on non-target organisms such as mammals, fish and beneficial insects to complete the present invention.

That is, the present invention relates to [1] to [14].

[1] A substituted isoxazoline compound or a substituted enone oxime compound represented by General Formula (1) or General Formula (2):

(where A¹, A², A³ and A⁴ independently represent a carbon atom or a nitrogen atom,

G¹ represents a benzene ring, a nitrogen-containing 6-membered aromatic heterocyclic ring, a furan ring, a thiophene ring or a 5-membered aromatic heterocyclic ring containing two or more heteroatoms selected from an oxygen atom, a sulfur atom and a nitrogen atom,

G² represents a structure represented by G²-1 to G²-11:

W represents an oxygen atom or a sulfur atom,

L represents —C(R^(4a))(R^(4b))—, —C(R^(4a))(R^(4b))CH₂—, —CH₂C(R^(4a))(R^(4b))—, —N(R^(4c))—, —C(R^(4a))(R^(4b))N(R^(4c))— or a single bond,

X represents a halogen atom, a cyano, a nitro, an azide, —SCN, —SF₅, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R⁴, a C₃ to C₈ cycloalkyl, a (C₃ to C₈) cycloalkyl optionally substituted with R⁴, E1 to E19, a C₂ to C₆ alkenyl, a (C₂ to C₆) alkenyl optionally substituted with R⁴, a C₅ to C₁₃ cycloalkenyl, a C₅ to C₁₀ halocycloalkenyl, a C₂ to C₆ alkynyl, a (C₂ to C₆) alkynyl optionally substituted with R⁴, —OH, —OR⁵, —OS(O)₂R⁵, —SH, —S(O)_(r)R⁵, —N(R⁷)R⁶, —N═C(R^(7a))R^(6a), —C(O)R⁸, —C(R⁸)═NOH, —C(R⁸)═NOR⁹, M3, M13, M30, —C(O)OR⁹, —C(O)SR⁹, —C(O)NH₂, —C(O)N(R¹⁰)R⁹, —C(S)OR⁹, —C(S)SR⁹, —C(S)NH₂, —C(S)N(R¹⁰)R⁹, M23 to M26, M28, M29, —S(O)₂OR⁹, —S(O)₂NH₂, —S(O)₂N(R¹⁰)R⁹, —Si(R^(11a))(R^(11b))R¹¹, a phenyl, a phenyl substituted with (Z)_(p1) or D1 to D38, where when m represents an integer of 2 or more, Xs may be the same as or different from each other,

and further, when two Xs are adjacent to each other, the two Xs adjacent to each other may form —CH₂CH₂CH₂—, —CH₂CH₂O—, —CH₂OCH₂—, —OCH₂O—, —CH₂CH₂S—, —CH₂SCH₂—, —CH₂CH₂N(R¹²)—, —CH₂N(R¹²)CH₂—, —CH₂CH₂CH₂CH₂—, —CH₂CH₂CH₂O—, —CH₂CH₂OCH₂—, —CH₂OCH₂O—, —OCH₂CH₂O—, —OCH₂CH₂S—, —CH₂CH═CH—, —OCH═CH—, —SCH═CH—, —N(R¹²)CH═CH—, —OCH═N—, —SCH═N—, —N(R¹²)CH═N—, —N(R¹²)N═CH—, —CH═CHCH═CH—, —OCH₂CH═CH—, —N═CHCH═CH—, —N═CHCH═N— or —N═CHN═CH— to form together with carbon atoms to which each of the two Xs is bonded, a 5-membered ring or a 6-membered ring, and in this case, a hydrogen atom bonded to each carbon atom forming the ring may be optionally replaced by Z, and further when hydrogen atoms are replaced simultaneously by 2 or more Zs, Zs may be the same as or different from each other,

Y represents a halogen atom, a cyano, a nitro, an azide, —SCN, —SF₅, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R⁴, a C₃ to C₈ cycloalkyl, a (C₃ to C₈) cycloalkyl optionally substituted with R⁴, E1 to E18, a C₂ to C₆ alkenyl, a (C₂ to C₆) alkenyl optionally substituted with R⁴, a C₂ to C₆ alkynyl, a (C₂ to C₆) alkynyl optionally substituted with R⁴, —OH, —OR⁵, —OS(O)₂R⁵, —SH, —S(O)_(r)R⁵, —NH₂, —N(R⁷)R⁶, —N(R⁷)C(O)R^(8a), —N═C(R^(7a))R^(6a), —C(O)NH₂, —C(O)N(R¹⁰)R⁹, —C(S)NH₂, —C(S)N(R¹⁰)R⁹, —Si(R^(11a))(R^(11b))R¹¹, a phenyl, a phenyl substituted with (Z)_(p1) or D1 to D38, where when n represents an integer of 2 or more, Ys may be the same as or different from each other,

and further, when two Ys are adjacent to each other, the two Ys adjacent to each other may form —CH₂CH₂CH₂—, —CH₂CH₂O—, —CH₂OCH₂—, —OCH₂O—, —CH₂CH₂S—, —CH₂SCH₂—, —SCH₂S—, —CH₂CH₂CH₂CH₂—, —CH₂CH₂CH₂O—, —CH₂CH₂OCH₂—, —CH₂OCH₂O—, —OCH₂CH₂O—, —OCH₂CH₂S—, —SCH₂CH₂S—, —OCH═N—, —SCH═N—, —CH═CHCH═CH—, —CH═CHCH═N—, —CH═CHN═CH—, —CH═NCH═CH— or —N═CHCH═CH— to form together with carbon atoms to which each of the two Ys is bonded, a 5-membered ring or a 6-membered ring, and in this case, a hydrogen atom bonded to each carbon atom forming the ring may be optionally replaced by Z, further when hydrogen atoms are replaced simultaneously by 2 or more Zs, Zs may be the same as or different from each other,

Z^(a) represents a halogen atom, a cyano, a nitro, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R⁴, —OH, —OR⁵, —OS(O)₂R⁵, —SH, —S(O)_(r)R⁵, —NH₂, —N(R⁷)R⁶, —C(O)R⁸, —C(R⁸)═NOH, —C(R⁸)═NOR⁹, M3, M13, M30, —C(O)OR⁹, —C(O)SR⁹, —C(O)N(R²)R¹, —C(S)OR⁹, —C(S)SR⁹, —C(S)N(R²)R¹, M23 to M26, M28, M29, —S(O)₂OR⁹, —S(O)₂NH₂, —S(O)₂N(R¹⁰)R⁹, —Si(R^(11a))(R^(11b))R¹¹, a phenyl or a phenyl substituted with (Z)_(p1), where when p represents an integer of 2 or more, Z^(a)s may be the same as or different from each other,

and further, when two Z^(a)s are adjacent to each other, the two Z^(a) adjacent to each other may form —CH═CH—CH═CH— to form a fused ring, in this case, a hydrogen atom bonded to each carbon atom forming the ring may be optionally replaced by a halogen atom, a cyano group, a nitro group, a C₁ to C₄ alkyl group, a C₁ to C₄ haloalkyl group, a C₁ to C₄ alkoxy group or a C₁ to C₄ alkylthio group,

R¹ represents a hydrogen atom, a cyano, a C₁ to C₁₂ alkyl, a (C₁ to C₁₂) alkyl optionally substituted with R¹³, a C₃ to C₁₂ cycloalkyl, a (C₃ to C₁₂) cycloalkyl optionally substituted with R¹³, E2 to E6, E9, E12 to E15, E18, a C₂ to C₁₂ alkenyl, a (C₂ to C₁₂) alkenyl optionally substituted with R¹³, a C₅ to C₁₄ cycloalkenyl, a C₅ to C₁₄ halocycloalkenyl, a C₃ to C₁₂ alkynyl, a (C₃ to C₁₂) alkynyl optionally substituted with R¹³, a C₃ to C₁₂ alkenyl, —C(O)R¹⁴, —C(R¹⁴)═NOH, —C(R¹⁴)═NOR¹⁵, M3, M13, M30, —C(R¹⁴)═NN(R¹⁷)R¹⁶, —C(O)OR¹⁵, —C(O)N(R¹⁷)R¹⁶, —C(O)N(R¹⁷)OR¹⁵, —C(O)N(R¹⁷)N(R¹⁷)R¹⁶, —C(S)R¹⁴, —C(S)OR¹⁵, —C(S)SR¹⁵, —C(S)N(R¹⁷)R¹⁶, —C(═NR¹⁶)OR¹⁵, —C(═NOR¹⁵)OR¹⁵, M7, M17, M23, M26, —C(═NR¹⁶)SR¹⁵, M9, M19, M24, M28, —C(═NR¹⁶)N(R¹⁷)R¹⁶, —C(═NCN)N(R¹⁷)R¹⁶, —C(═NOR¹⁵)N(R¹⁷)R¹⁶, —C(═NNO₂)N(R¹⁷)R¹⁶, M11, M21, M25, M29, —OR¹⁵, —SR¹⁵, —S(O)₂R¹⁵, —S(O)₂N(R¹⁷)R¹⁶, —N(R¹⁷)R¹⁶, —N═C(R^(17a))R^(16a), —C(O)ON═C(R^(17a))R^(16a), —SN(R¹⁹)R¹⁸, a phenyl, a phenyl substituted with (Z)_(p1), D1 to D25 or D27 to D38,

R² represents a hydrogen atom, a cyano, a C₁ to C₁₂ alkyl, a (C₁ to C₁₂) alkyl optionally substituted with R^(13a), a C₃ to C₁₂ cycloalkyl, a C₃ to C₁₂ alkenyl, a C₃ to C₁₂ haloalkenyl, a C₅ to C₁₄ cycloalkenyl, a C₅ to C₁₄ halocycloalkenyl, C₃ to C₁₂ alkynyl, a C₃ to C₁₂ haloalkynyl, —C(O)R^(14a), —C(O)OR^(15a), —C(O)SR^(15a), —C(O)N(R¹⁷)R¹⁶, —C(O)C(O)OR^(15a), —C(S)OR^(15a), —C(S)SR^(15a), —C(S)N(R¹⁷)R¹⁶, —OR¹⁵, —SR¹⁵, —N(R¹⁷)R¹⁶, —N═C(R^(17a))R^(16a), —S(O)₂R^(15a), —S(O)₂N(R¹⁷)R¹⁶, —SN(R¹⁹)R¹⁸, a phenyl, a phenyl substituted with (Z)_(p1), D1, D2 or D32 to D35, or R² together with R¹ may form ═C(R^(2b))R^(1b) or a C₂ to C₇ alkylene chain to form together with a nitrogen atom to which R¹ and R² are bonded, a 3- to 8-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom and may be optionally substituted with a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₆ haloalkyl group, a C₁ to C₆ alkoxy(C₁ to C₆) alkyl group, a C₁ to C₆ alkoxy group, a —CHO group, a C₁ to C₆ alkylcarbonyl group, a C₁ to C₆ haloalkylcarbonyl group, a C₁ to C₆ alkoxycarbonyl group, a C₁ to C₆ haloalkoxycarbonyl group, a C₁ to C₆ alkylaminocarbonyl group, a C₁ to C₆ haloalkylaminocarbonyl group, a phenyl group, a phenyl substituted with (Z)_(p1), a D32 group, a D33 group, a D34 group, a D35 group, an oxo group or a thioxo group,

and further, when the substituent Y is present adjacent to G², R² together with Y may form —CH₂—, —CH₂CH₂—, —CH₂O—, —CH₂S—, —CH₂N(R⁶)—, —CH═CH— or —CH═N— to form together with atoms to which each of R² and Y is bonded, a 5-membered ring or a 6-membered ring, and in this case, a hydrogen atom bonded to each carbon atom forming the ring may be optionally replaced by a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₆ haloalkyl group, a C₁ to C₆ alkylidene group, a C₁ to C₆ haloalkylidene group, an oxo group or a thioxo group,

R^(1a) represents —C(O)R¹⁴, —C(O)OR¹⁵, —C(O)SR¹⁵, —C(O)N(R¹⁷)R¹⁶, —C(O)N(R¹⁷)OR¹⁵, —C(O)N(R¹⁷)N(R¹⁷)R¹⁶, —C(S)R¹⁴, —C(S)OR¹⁵, —C(S)SR¹⁵, —C(S)N(R¹⁷)R¹⁶, —C(SR¹⁵)═NCN, —C(SR¹⁵)═NNO₂, —S(O)₂R¹⁵ or —S(O)₂N(R¹⁷)R¹⁶,

R^(2a) represents a hydrogen atom, a cyano, a C₁ to C₁₂ alkyl, a (C₁ to C₁₂) alkyl optionally substituted with R^(13a), a C₃ to C₁₂ cycloalkyl, a C₃ to C₁₂ alkenyl, a C₃ to C₁₂ haloalkenyl, a C₃ to C₁₂ alkynyl, a C₃ to C₁₂ haloalkynyl, —C(O)R^(14a), —C(O)OR^(15a), —C(O)SR^(15a), —C(O)N(R¹⁷)R¹⁶, —C(O)C(O)OR^(15a), —C(S)OR^(15a), —C(S)SR^(15a), —C(S)N(R¹⁷) R¹⁶, a C₁ to C₁₂ alkoxy, a C₁ to C₁₂ haloalkoxy, —SR¹⁵, —S(O)₂R^(15a), —SN(R¹⁹)R¹⁸, a phenyl, a phenyl substituted with (Z)_(p1), D1, D2 or D32 to D35, or R^(2a) together with R^(1a) may form a C₃ to C₆ alkylene chain to form together with a nitrogen atom to which R^(1a) and R^(2a) are bonded, a 4- to 7-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom and may be optionally substituted with a C₁ to C₆ alkyl group, a C₁ to C₆ alkylidene group, a —CHO group, a C₁ to C₆ alkylcarbonyl group, a C₁ to C₆ haloalkylcarbonyl group, a C₁ to C₆ alkoxycarbonyl group, a C₁ to C₆ haloalkoxycarbonyl group, a C₁ to C₆ alkylaminocarbonyl group, a C₁ to C₆ haloalkylaminocarbonyl group, a di(C₁ to C₆ alkyl)aminocarbonyl group, a phenyl group, a D32 group, a D34 group, an oxo group or a thioxo group,

R^(1b) represents a hydrogen atom, R¹⁴, —OR¹⁵, —SR¹⁵, —S(O)₂R¹⁵ or —N(R^(17b))R^(16b),

R^(2b) represents a C₁ to C₆ alkyl, —OR^(15a), —SR^(15a), —SC(O)R^(14a), —SC(O)OR^(15a) or —N(R^(17c))R^(16c), or R^(2b) together with R^(1b) may form a C₄ to C₅ alkylene chain or a C₄ to C₅ alkenylene chain to form together with a carbon atom to which R^(1b) and R^(2b) are bonded, a 5- or 6-membered ring, and in this case, the alkylene chain or the alkenylene chain may contain one to three oxygen atom(s), sulfur atom(s) or nitrogen atom(s) and may be optionally substituted with a halogen atom, a cyano group, a nitro group, a C₁ to C₆ alkyl group, a C₁ to C₆ haloalkyl group, a C₁ to C₆ alkoxy group, a C₁ to C₆ haloalkoxy group, a C₁ to C₆ alkylthio group, a C₁ to C₆ haloalkylthio group or a R^(17c) group,

R³ represents a halogen atom, a cyano, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R⁴, a C₃ to C₈ cycloalkyl, a (C₃ to C₈) cycloalkyl optionally substituted with R⁴, E1 to E19, a C₃ to C₆ alkenyl, a (C₂ to C₆) alkenyl optionally substituted with R⁴, a C₃ to C₆ alkynyl, a (C₂ to C₆) alkynyl optionally substituted with R⁴, —OR⁵, —S(O)_(r)R⁵, —N(R¹⁰)R⁹, —C(O)R⁸, —C(R⁸)═NOH, —C(R⁸)═NOR⁹, M3, M13, M30, —C(O)OR⁹, —C(O)SR⁹, —C(O)NH₂, —C(O)N(R¹⁰)R⁹, —C(S)OR⁹, —C(S)SR⁹, —C(S)NH₂, —C(S)N(R¹⁰)R⁹, —Si(R^(11a))(R^(11b))R¹¹, —P(O)(OR²⁰)₂, a phenyl, a phenyl substituted with (Z)_(p1) or D1 to D38,

R^(3a) represents a halogen atom, a cyano, a nitro, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R⁴, a C₃ to C₈ cycloalkyl, a C₂ to C₆ alkenyl, a C₂ to C₆ alkynyl, —C(O)OR⁹, —C(O)SR⁹, —C(O)NH₂, —C(O)N(R¹⁰)R⁹, —C(S)OR⁹, —C(S)SR⁹, —C(S)NH₂, —C(S)N(R¹⁰)R⁹, a C₁ to C₆ alkylthio, a C₁ to C₆ haloalkylthio or a phenyl,

R^(3b) represents a hydrogen atom, a halogen atom, a C₁ to C₆ alkyl, a C₃ to C₆ haloalkyl, a C₃ to C₆ alkenyl or a C₃ to C₆ alkynyl,

R^(3c) represents a hydrogen atom or R^(3a),

D1 to D38 individually represent an aromatic heterocyclic ring represented by the following Structural Formulae:

Z represents a halogen atom, a cyano, a nitro, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₁ to C₄ alkoxy(C₁ to C₄) alkyl, a C₁ to C₄ haloalkoxy(C₁ to C₄) alkyl, a C₁ to C₄ alkylthio(C₁ to C₄) alkyl, a C₁ to C₄ haloalkylthio(C₁ to C₄) alkyl, a C₁ to C₄ alkylsulfinyl(C₁ to C₄) alkyl, a C₁ to C₄ haloalkylsulfinyl(C₁ to C₄) alkyl, a C₁ to C₄ alkylsulfonyl(C₁ to C₄) alkyl, a C₁ to C₄ haloalkylsulfonyl(C₁ to C₄) alkyl, a C₃ to C₆ cycloalkyl, a C₃ to C₆ halocycloalkyl, —OH, a C₁ to C₆ alkoxy, a C₁ to C₆ haloalkoxy, a C₁ to C₆ alkyl sulfonyloxy, a C₁ to C₆ haloalkylsulfonyloxy, a C₁ to C₆ alkylthio, a C₁ to C₆ haloalkylthio, a C₁ to C₆ alkylsulfinyl, a C₁ to C₆ haloalkylsulfinyl, a C₁ to C₆ alkylsulfonyl, a C₁ to C₆ haloalkylsulfonyl, —NH₂, a C₁ to C₆ alkylamino, a di(C₁ to C₆ alkyl)amino, a C₁ to C₆ alkoxycarbonyl, a C₁ to C₆ haloalkoxycarbonyl, —C(O)NH₂, a C₁ to C₆ alkylaminocarbonyl, a C₁ to C₆ haloalkylaminocarbonyl, a di(C₁ to C₆ alkyl)aminocarbonyl, —C(S)NH₂, —S(O)₂NH₂, a C₁ to C₆ alkylaminosulfonyl, a di(C₁ to C₆ alkyl)aminosulfonyl, a phenyl or a phenyl optionally substituted with a halogen atom, where when p and p1 individually represent an integer of 2 or more, Zs may be the same as or different from each other, and further, when two Zs are adjacent to each other, the two Zs adjacent to each other may form —CH₂CH₂CH₂—, —CH₂CH₂O—, —CH₂OCH₂—, —OCH₂O—, —CH₂CH₂S—, —CH₂SCH₂—, —CH₂CH₂CH₂CH₂—, —CH₂CH₂CH₂O—, —CH₂CH₂OCH₂—, —CH₂OCH₂O—, —OCH₂CH₂O—, —CH₂CH₂CH₂S—, —OCH₂CH₂S— or —CH═CH—CH═CH— to form together with carbon atoms to which each of the two Zs is bonded, a 5-membered ring or a 6-membered ring, and in this case, a hydrogen atom bonded to each carbon atom forming the ring may be optionally replaced by a halogen atom, a cyano group, a nitro group, a C₁ to C₄ alkyl group, a C₁ to C₄ haloalkyl group, a C₁ to C₄ alkoxy group or a C₁ to C₄ alkylthio group,

E1 to E19 individually represent a saturated heterocyclic ring represented by the following Structural Formulae:

R⁴ represents a halogen atom, a cyano, a C₃ to C₈ cycloalkyl, a C₃ to C₈ halocycloalkyl, E1 to E19, —OH, —OR⁵, —SH, —S(O)_(r)R⁵, —N(R⁷)R⁶, —N(R⁷)C(O)R^(8a), —C(O)OR⁹, —C(O)N(R¹⁰)R⁹, —Si(R^(11a))(R^(11b))R¹¹, a phenyl, a phenyl substituted with (Z)_(p1) or D1 to D38,

R^(4a) represents a hydrogen atom, a cyano, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₃ to C₆ cycloalkyl, a C₂ to C₆ alkenyl, a C₂ to C₄ alkynyl, a C₁ to C₆ alkoxycarbonyl, —C(O)NH₂, —C(S)NH₂, a phenyl, a phenyl substituted with (Z)_(p1), D1, D2, D9, D10 or D32,

R^(4b) represents a hydrogen atom or a C₁ to C₆ alkyl, or R^(4b) together with R^(4a) may form a C₂ to C₅ alkylene chain to form together with a carbon atom to which R^(4a) and R^(4b) are bonded, a 3- to 6-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom and may be optionally substituted with a C₁ to C₆ alkyl group, a —CHO group, a C₁ to C₆ alkylcarbonyl group, a C₁ to C₆ alkoxycarbonyl group, a C₁ to C₆ alkylaminocarbonyl group, a C₁ to C₆ haloalkylaminocarbonyl group or a phenyl group,

R^(4c) represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₁ to C₆ alkylcarbonyl, a C₁ to C₆ haloalkylcarbonyl, a C₃ to C₆ cycloalkylcarbonyl, a C₃ to C₆ halocycloalkylcarbonyl, a C₁ to C₆ alkoxycarbonyl or a C₁ to C₆ haloalkoxycarbonyl,

R⁵ represents a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R²³, a C₃ to C₈ cycloalkyl, a (C₃ to C₈) cycloalkyl optionally substituted with R²³, E2 to E6, E12 to E15, E18, a C₂ to C₆ alkenyl, a (C₂ to C₆) alkenyl optionally substituted with R²³, a C₅ to C₁₀ cycloalkenyl, a C₅ to C₁₀ halocycloalkenyl, a C₃ to C₆ alkynyl, a (C₃ to C₆) alkynyl optionally substituted with R²³, a C₁ to C₆ alkylcarbonyl, a C₁ to C₆ alkoxycarbonyl, a phenyl, a phenyl substituted with (Z)_(p1), D1, D2, D4 to D6, D8 to D10, D12 to D19, D21, D23, D25, D27 or D30 to D38,

R⁶ represents a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R²³, a C₃ to C₈ cycloalkyl, a C₃ to C₈ halocycloalkyl, a C₃ to C₆ alkenyl, a C₃ to C₆ haloalkenyl, a C₃ to C₆ alkynyl, a C₃ to C₆ haloalkynyl, —C(O)R⁸, —C(O)OR⁹, —C(O)SR⁹, —C(O)NH₂, —C(O)N(R¹⁹)R⁹, —C(S)OR⁹, —C(S)SR⁹, —C(S)NH₂, —C(S)N(R¹⁰)R⁹, —C(O)C(O)R⁹, —C(O)C(O)OR⁹, —OH, —S(O)₂R⁹, —S(O)₂N(R¹⁰)R⁹, —P(O)(OR²⁹)₂ or —P(S)(OR²⁰)₂,

R⁷ represents a hydrogen atom, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R²³, a C₃ to C₈ cycloalkyl, a C₃ to C₆ alkenyl, a C₃ to C₆ haloalkenyl, a C₃ to C₆ alkynyl, a C₃ to C₆ haloalkynyl, —CHO, a C₁ to C₆ alkylcarbonyl, a C₁ to C₆ haloalkylcarbonyl or a C₁ to C₆ alkoxycarbonyl, or R⁷ together with R⁶ may form a C₂ to C₆ alkylene chain to form together with a nitrogen atom to which R⁶ and R⁷ are bonded, a 3- to 7-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom and may be optionally substituted with a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₆ haloalkyl group, an oxo group or a thioxo group,

R^(6a) represents a C₁ to C₆ alkyl, a C₁ to C₆ alkoxy, a C₁ to C₆ haloalkoxy, a C₃ to C₆ alkenyloxy, a phenoxy or a phenoxy substituted with (Z)_(p1),

R^(7a) represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₃ to C₆ alkenyl, a phenyl or a phenyl substituted with (Z)_(p1), or R^(7a) together with R^(6a) may form a C₄ to C₆ alkylene chain to form together with a carbon atom to which R^(6a) and R^(7a) are bonded, a 5- to 7-membered ring, and in this case, the alkylene chain may contain one oxygen atom or sulfur atom,

R⁸ represents a hydrogen atom, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R²³, a C₃ to C₈ cycloalkyl, a C₃ to C₈ halocycloalkyl, E4 to E6, E12 to E14, a C₃ to C₆ alkenyl, a C₃ to C₆ haloalkenyl, a C₅ to C₁₀ cycloalkenyl, a C₅ to C₁₀ halocycloalkenyl, a C₃ to C₆ alkynyl or a C₃ to C₆ haloalkynyl,

R^(8a) represents a phenyl, a phenyl substituted with (Z)_(p1), or D1 to D38,

R⁹ represents a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R²³, a C₃ to C₈ cycloalkyl, a C₃ to C₈ halocycloalkyl, E2 to E6, E12 to E19, a C₃ to C₆ alkenyl, a C₃ to C₆ haloalkenyl, a C₃ to C₆ alkynyl, a C₃ to C₆ haloalkynyl, a phenyl, a phenyl substituted with (Z)_(p1), D1 to D25 or D27 to D38,

R¹⁰ represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₃ to C₆ cycloalkyl(C₁ to C₄) alkyl, a C₁ to C₆ alkoxy(C₁ to C₄) alkyl, a C₁ to C₆ alkylthio(C₁ to C₄) alkyl, a cyano(C₁ to C₆) alkyl, a C₃ to C₆ alkenyl or a C₃ to C₆ alkynyl, or R¹⁰ together with R⁹ may form a C₂ to C₆ alkylene chain to form together with a nitrogen atom to which R⁹ and R¹⁰ are bonded, a 3- to 7-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom and may be optionally substituted with a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₆ alkoxy group, a —CHO group, a C₁ to C₆ alkylcarbonyl group or a C₁ to C₆ alkoxycarbonyl group,

R¹¹ represents a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₁ to C₆ alkoxy, a phenyl or a phenyl substituted with (Z)_(p1),

R^(11a) and R^(11b) independently represent a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl or a C₁ to C₆ alkoxy,

R¹² represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₁ to C₆ alkoxycarbonyl(C₁ to C₄) alkyl, a C₁ to C₆ haloalkoxycarbonyl(C₁ to C₄) alkyl, a phenyl(C₁ to C₄) alkyl, a phenyl(C₁ to C₄) alkyl substituted with (Z)_(p1), a C₂ to C₆ alkenyl, a C₂ to C₆ haloalkenyl, a C₃ to C₆ alkynyl, a C₃ to C₆ haloalkynyl, a C₁ to C₆ alkoxy, a C₁ to C₆ alkoxylcarbonyl, a C₁ to C₆ haloalkoxycarbonyl, a phenyl or a phenyl substituted with (Z)_(p1),

and further, when Z is present adjacent to R¹², R¹² and Z adjacent to each other may form —CH₂CH₂CH₂CH₂—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —CH═CH—N═CH— or —CH═CH—CH═N— to form together with atoms to which each of R¹² and Z is bonded, a 6-membered ring, and in this case, a hydrogen atom bonded to each carbon atom forming the ring may be optionally replaced by a halogen atom, a C₁ to C₄ alkyl group or a C₁ to C₄ haloalkyl group,

R¹³ and R^(13a) independently represent a halogen atom, a cyano, a nitro, a C₃ to C₈ cycloalkyl, a C₃ to C₈ halocycloalkyl, a hydroxy(C₃ to C₈) cycloalkyl, a C₁ to C₄ alkoxy(C₃ to C₈) cycloalkyl, E1 to E19, a C₅ to C₁₀ cycloalkenyl, a C₅ to C₁₀ halocycloalkenyl, —OR²⁴, —N(R²⁵)R²⁴, —SH, —S(O)_(r)R²⁶, —C(O)R²⁷, —C(R²⁷)═NOH, —C(R²⁷)═NOR²⁸, —C(O)OH, —C(O)OR²⁸, —C(O)SR²⁸, —C(O)NH₂, —C(O)N(R²⁹)R²⁸, —C(O)N(R²⁹)OR²⁸, —C(O)N(R²⁹)N(R²⁹)R²⁸, —C(O)C(O)OR²⁸, —C(S)OR²⁸, —C(S)SR²⁸, —C(S)NH₂, —C(S)N(R²⁹)R²⁸, —C(═NR²⁹)OR²⁸, —C(═NR²⁹)SR²⁸, —C(═NR²⁹)N(R²⁹)R²⁸, —C(═NOR²⁸)N(R²⁹)R²⁸, —S(O)₂OH, —S(O)₂NH₂, —S(O)₂N(R²⁹)R²⁸, —Si(R^(11a))(R^(11b))R¹¹, —P(O)(OR²⁰)₂, —P(S)(OR²⁰)₂, —P(phenyl)₂, —P(O)(phenyl)₂, M1 to M30, a phenyl, a phenyl substituted with (Z)_(p1), a naphthyl or D1 to D38,

M1 to M30 individually represent a partially saturated heterocyclic ring represented by the following Structural Formulae:

R¹⁴ and R^(14a) independently represent a hydrogen atom, a C₁ to C₁₂ alkyl, a (C₁ to C₁₂) alkyl optionally substituted with R³⁰, a C₃ to C₁₂ cycloalkyl, a (C₃ to C₁₂) cycloalkyl optionally substituted with R³⁰, E1 to E19, a C₂ to C₁₂ alkenyl, a (C₂ to C₁₂) alkenyl optionally substituted with R³⁰, a C₅ to C₁₂ cycloalkenyl, a C₅ to C₁₂ halocycloalkenyl, a C₂ to C₁₂ alkynyl, a (C₂ to C₁₂) alkynyl optionally substituted with R³⁰—C(R²⁷)═NOR²⁸, —C(R²⁷)═NN(R²⁹)R²⁸, —C(O)OR²⁸, —C(O)N(R²⁹)R²⁸, M4, a phenyl, a phenyl substituted with (Z)_(p1), a naphthyl or D1 to D38,

R¹⁵ and R^(15a) independently represent a C₁ to C₁₂ alkyl, a (C₁ to C₁₂) alkyl optionally substituted with R³⁰, a C₃ to C₁₂ cycloalkyl, a (C₃ to C₁₂) cycloalkyl optionally substituted with R³⁰, E2 to E6, E12 to E19, a C₂ to C₁₂ alkenyl, a C₂ to C₁₂ haloalkenyl, a C₅ to C₁₀ cycloalkenyl, a C₅ to C₁₀ halocycloalkenyl, a C₃ to C₁₂ alkynyl, a C₂ to C₁₂ haloalkynyl, a phenyl, a phenyl substituted with (Z)_(p1), D1, D2, D4 to D6, D8 to D10, D12 to D19, D21, D23, D25, D27 or D30 to D38,

R¹⁶ represents a hydrogen atom, a C₁ to C₁₂ alkyl, a (C₁ to C₁₂) alkyl optionally substituted with R³⁰, a C₃ to C₁₂ cycloalkyl, a (C₃ to C₁₂) cycloalkyl optionally substituted with R³⁰, E2 to E6, E12 to E19, a C₂ to C₁₂ alkenyl, a C₂ to C₁₂ haloalkenyl, a C₅ to C₁₀ cycloalkenyl, a C₅ to C₁₀ halocycloalkenyl, a C₃ to C₁₂ alkynyl, a C₂ to C₁₂ haloalkynyl, —C(O)R²⁷, —C(O)OR²⁸, —C(O)SR²⁸, —C(O)NH₂, —C(O)N(R²⁹)R²⁸, —C(S)R²⁷, —C(S)OR²⁸, —C(S)SR²⁸, —C(S)NH₂, —C(S)N(R²⁹)R²⁸, M7 M9, M17, M19, —S(O)₂R²⁸, —S(O)₂NH₂, —S(O)₂N(R²⁹)R²⁸, —P(O)(OR²⁰)₂, —P(S)(OR²)₂, a phenyl, a phenyl substituted with (Z)_(p1), D1 to D25 or D27 to D38,

R¹⁷ represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₃ to C₆ cycloalkyl(C₁ to C₄) alkyl, a C₁ to C₄ alkoxy(C₁ to C₄) alkyl, a C₁ to C₄ haloalkoxy(C₁ to C₄) alkyl, a C₁ to C₄ alkylthio(C₁ to C₄) alkyl, a C₁ to C₄ haloalkylthio(C₁ to C₄) alkyl, a C₁ to C₄ alkylsulfonyl(C₁ to C₄) alkyl, a C₁ to C₄ haloalkylsulfonyl(C₁ to C₄) alkyl, a cyano(C₁ to C₆) alkyl, a C₁ to C₄ alkoxycarbonyl(C₁ to C₄) alkyl, a phenyl(C₁ to C₄) alkyl, a C₂ to C₆ alkenyl, a C₂ to C₆ haloalkenyl, a C₃ to C₆ alkynyl or a C₃ to C₆ haloalkynyl, or R¹⁷ together with R¹⁶ may form a C₂ to C₆ alkylene chain to form together with a nitrogen atom to which R¹⁶ and R¹⁷ are bonded, a 3- to 7-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom and may be optionally substituted with a halogen atom, a C₁ to C₆ alkyl group,

a C₁ to C₄ alkoxy(C₁ to C₄) alkyl group, a C₁ to C₆ alkoxy group, a —CHO group, a C₁ to C₆ alkylcarbonyl group, a C₁ to C₆ alkoxycarbonyl group, an oxo group or a thioxo group,

R^(16a) represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₁ to C₄ alkoxy(C₁ to C₄) alkyl, a C₁ to C₄ alkylthio(C₁ to C₄) alkyl, a C₁ to C₄ alkylsulfonyl(C₁ to C₄) alkyl, a C₁ to C₄ alkoxycarbonyl(C₁ to C₄) alkyl, a phenyl(C₁ to C₄) alkyl, a phenyl(C₁ to C₄) alkyl substituted with (Z)_(p1), a C₃ to C₆ cycloalkyl, E1 to E19, a phenyl(C₂ to C₄) alkenyl, a di(C₁ to C₆ alkyl)amino, a phenyl, a phenyl substituted with (Z)_(p1) or D1 to D38,

R^(17a) represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ alkoxy, a C₁ to C₆ alkylthio or a di(C₁ to C₆ alkyl)amino, or R^(17a) together with R^(16a) may form a C₃ to C₅ alkylene chain to form together with a carbon atom to which R^(16a) and R^(17a) are bonded, a 4- to 6-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom and may be optionally substituted with a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₆ haloalkyl group, a —CHO group, a C₁ to C₆ alkylcarbonyl group or a C₁ to C₆ alkoxycarbonyl group,

R^(16b) represents a hydrogen atom, a cyano, a nitro, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl or a C₁ to C₆ alkoxy,

R^(17b) represents a hydrogen atom or a C₁ to C₆ alkyl, or R^(17b) together with R^(16b) may form a C₃ to C₅ alkylene chain to form together with a nitrogen atom to which R^(16b) and R^(17b) are bonded, a 4- to 6-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom and may be optionally substituted with a C₁ to C₆ alkyl group, a —CHO group, a C₁ to C₆ alkylcarbonyl group or a C₁ to C₆ alkoxycarbonyl group,

R^(16c) represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₃ to C₆ alkenyl, a C₃ to C₆ alkynyl, a C₁ to C₆ alkoxy, a C₁ to C₆ haloalkoxy, —NH₂, a C₁ to C₆ alkylamino, a di(C₁ to C₆ alkyl)amino, —NHC(O)R²⁷, —NHC(O)OR²⁸, —NHC(O)SR²⁸, —NHC(O)NH₂, —NHC(O)N(R²⁹)R²⁸, —NHC(S)OR²⁸, —NHC(S)SR²⁸, —NHC(S)NH₂, —NHC(S)N(R²⁹)R²⁸, —NHS(O)₂R²⁸, —NHS(O)₂NH₂ or —NHS(O)₂N(R²⁹)R²⁸,

R^(17c) represents a hydrogen atom or a C₁ to C₆ alkyl, or R^(17c) together with R^(16c) may form a C₃ to C₅ alkylene chain to form together with a nitrogen atom to which R^(16c) and R^(17c) are bonded, a 4- to 6-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom and may be optionally substituted with a C₁ to C₆ alkyl group, a —CHO group, a C₁ to C₆ alkylcarbonyl group or a C₁ to C₆ alkoxycarbonyl group,

R¹⁸ represents a C₁ to C₁₂ alkyl, a C₁ to C₁₂ haloalkyl, a C₁ to C₁₂ alkoxy(C₁ to C₁₂) alkyl, a cyano(C₁ to C₁₂) alkyl, a C₁ to C₁₂ alkoxycarbonyl(C₁ to C₁₂) alkyl, a phenyl(C₁ to C₄) alkyl, a phenyl(C₁ to C₄) alkyl substituted with (Z)_(p1), a C₃ to C₁₂ alkenyl, a C₃ to C₁₂ haloalkenyl, a C₃ to C₁₂ alkynyl, a C₃ to C₁₂ haloalkynyl, a C₁ to C₁₂ alkylcarbonyl, a C₁ to C₁₂ alkoxycarbonyl, —C(O)ON═C(CH₃)SCH₃, —C(O)ON═C(SCH₃)C(O)N(CH₃)₂, a phenyl or a phenyl substituted with (Z)_(p1),

R¹⁹ represents a C₁ to C₁₂ alkyl, a C₁ to C₁₂ haloalkyl, a C₁ to C₁₂ alkoxy(C₁ to C₁₂) alkyl, a cyano(C₁ to C₁₂) alkyl, a C₁ to C₁₂ alkoxycarbonyl(C₁ to C₁₂) alkyl, a phenyl(C₁ to C₄)alkyl, a phenyl(C₁ to C₄) alkyl substituted with (Z)_(p1), a C₃ to C₁₂ alkenyl, a C₃ to C₁₂ haloalkenyl, a C₃ to C₁₂ alkynyl, a C₃ to C₁₂ haloalkynyl, a phenyl or a phenyl substituted with (Z)_(p1), or R¹⁹ together with R¹⁸ may form a C₄ to C₇ alkylene chain to form together with a nitrogen atom to which R¹⁸ and R¹⁹ are bonded, a 5- to 8-membered ring, and in this case, the alkylene chain may contain one oxygen atom or sulfur atom and may be optionally substituted with a C₁ to C₄ alkyl group or a C₁ to C₄ alkoxy group,

R²⁰ represents a C₁ to C₆ alkyl or a C₁ to C₆ haloalkyl,

R²¹ represents a halogen atom, a cyano, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a hydroxy(C₁ to C₆) alkyl, a C₁ to C₄ alkoxy(C₁ to C₄) alkyl, a C₁ to C₄ alkoxycarbonyl(C₁ to C₄)alkyl, a C₁ to C₆ alkoxy, a C₁ to C₆ alkylthio, a C₁ to C₆ alkylamino, a di(C₁ to C₄ alkyl)amino, a C₁ to C₆ alkoxycarbonyl, a phenyl or a phenyl substituted with (Z)_(p1), where when q represents an integer of 2 or more, R²¹s may be the same as or different from each other, and further when two R²¹s are replaced on the same carbon atom, the two R²¹s together with each other may form an oxo, a thioxo, an imino, a C₁ to C₆ alkylimino, a C₁ to C₆ alkoxyimino or a C₁ to C₆ alkylidene,

R²² represents a hydrogen atom, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R³⁰, a C₃ to C₆ cycloalkyl, a C₃ to C₆ alkenyl, a C₃ to C₆ haloalkenyl, a C₃ to C₆ alkynyl, —OH, a benzyloxy, —C(O)R³¹, —C(O)OR³², —C(O)SR³², —C(O)N(R³⁴)R³³, —C(S)N(R³⁴)R³³, —S(O)₂R³², —P(O)(OR²⁰)₂, —P(S)(OR²⁰)₂, a phenyl, a phenyl substituted with (Z)_(p1) or D3,

R²³ represents a halogen atom, a cyano, a C₃ to C₈ cycloalkyl, a C₃ to C₈ halocycloalkyl, E1 to E19, a C₁ to C₆ alkoxy, a C₁ to C₆ haloalkoxy, a C₁ to C₆ alkylthio, a C₁ to C₆ haloalkylthio, a C₁ to C₆ alkylsulfonyl, a C₁ to C₆ haloalkylsulfonyl, a C₁ to C₆ alkylamino, a di(C₁ to C₆ alkyl)amino, —CHO, a C₁ to C₆ alkylcarbonyl, a C₁ to C₆ haloalkylcarbonyl, a C₁ to C₆ alkoxycarbonyl, a C₁ to C₆ haloalkoxycarbonyl, a C₁ to C₆ alkylaminocarbonyl, a di(C₁ to C₆ alkyl)aminocarbonyl, a phenyl, a phenyl substituted with (Z)_(p1) or D1 to D38,

R²⁴ represents a hydrogen atom, a C₁ to C₈ alkyl, a (C₁ to C₈) alkyl optionally substituted with R³⁰, a C₃ to C₈ cycloalkyl, a (C₃ to C₈) cycloalkyl optionally substituted with R³⁰, E2 to E6, E12 to E19, a C₃ to C₈ alkenyl, a (C₃ to C₈) alkenyl optionally substituted with R³⁰, a C₃ to C₈ alkynyl, a (C₃ to C₈) alkynyl optionally substituted with R³⁰, —C(O)R³¹, —C(O)OR³², —C(O)SR³², —C(O)N(R³⁴)R³³, —C(O)C(O)R³², —C(O)C(O)OR³², —C(S)R³¹, —C(S)OR³², —C(S)SR³², —C(S)N(R³⁴)R³³, —S(O)₂R³², S(O)₂N(R³⁴)R³³, —Si(R^(11a))(R^(11b))R¹¹, —P(O)(OR²⁰)₂, —P(S)(OR²⁰)₂, a phenyl, a phenyl substituted with (Z)_(p1), D1, D2, D4 to D6, D8 to D10, D12 to D19, D21, D23, D25, D27 or D30 to D38,

R²⁵ represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₁ to C₄ alkoxy(C₁ to C₄) alkyl, a C₁ to C₄ alkylthio(C₁ to C₄) alkyl, a C₃ to C₆ cycloalkyl, a C₃ to C₆ alkenyl, a C₃ to C₆ alkynyl, a C₁ to C₆ alkoxy, a phenyl or a phenyl substituted with (Z)_(p1), or R²⁵ together with R²⁴ may form a C₂ to C₅ alkylene chain to form together with a nitrogen atom to which R²⁴ and R²⁵ are bonded, a 3- to 6-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom and may be substituted with a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₆ haloalkyl group, a C₁ to C₆ alkoxy group, a —CHO group, a C₁ to C₆ alkylcarbonyl group, a C₁ to C₆ alkoxycarbonyl group, a phenyl group, a phenyl group substituted with (Z)_(p1), an oxo group or a thioxo group,

R²⁶ represents a C₁ to C₈ alkyl, a (C₁ to C₈) alkyl optionally substituted with R³⁰, a C₃ to C₈ cycloalkyl, a (C₃ to C₈) cycloalkyl optionally substituted with R³⁰, E2 to E6, E12 to E19, a C₃ to C₈ alkenyl, a (C₃ to C₈) alkenyl optionally substituted with R³⁰, a C₃ to C₈ alkynyl, a (C₃ to C₈) alkynyl optionally substituted with R³⁰, —C(O)R³¹, —C(O)OR³², —C(O)SR³², —C(O)N(R³⁴)R³³, —C(O)C(O)R³², —C(O)C(O)OR³², —C(S)R³¹, —C(S)OR³², —C(S)SR³², —C(S)N(R³⁴)R³³, —SH, a C₁ to C₆ alkylthio, a C₁ to C₆ haloalkylthio, a phenylthio, a phenylthio substituted with (Z)_(p1), —P(O)(OR²⁰)₂, —) P(S)(OR²⁰)₂, a phenyl, a phenyl substituted with (Z)_(p1), D9, D10, D12, D14 to D17, D30, D32 or D34,

R²⁷ represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₃ to C₆ cycloalkyl(C₁ to C₄) alkyl, a C₁ to C₆ alkoxy(C₁ to C₄) alkyl, a C₁ to C₆ haloalkoxy(C₁ to C₄) alkyl, a C₁ to C₆ alkylthio(C₁ to C₄) alkyl, a C₁ to C₆ haloalkylthio(C₁ to C₄) alkyl, a C₁ to C₆ alkylsulfonyl(C₁ to C₄) alkyl, a C₁ to C₆ haloalkylsulfonyl(C₁ to C₄) alkyl, a phenyl(C₁ to C₄) alkyl, a phenyl(C₁ to C₄) alkyl substituted with (Z)_(p1), a C₃ to C₆ cycloalkyl, a phenyl or a phenyl substituted with (Z)_(p1),

R²⁸ represents a C₁ to C₈ alkyl, a (C₁ to C₈) alkyl optionally substituted with R³⁰, a C₃ to C₈ cycloalkyl, a (C₃ to C₈) cycloalkyl optionally substituted with R³⁰, E1 to E7, E12 to E19, a C₂ to C₈ alkenyl, a (C₂ to C₈) alkenyl optionally substituted with R³⁰, a C₃ to C₈ alkynyl, a (C₃ to C₈) alkynyl optionally substituted with R³⁰, a phenyl, a phenyl substituted with (Z)_(p1), D1 to D25 or D27 to D38,

R²⁹ represents a hydrogen atom, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R³⁰, a C₃ to C₆ alkenyl, a C₃ to C₆ haloalkenyl, a C₃ to C₆ alkynyl, a C₃ to C₆ haloalkynyl, a phenyl or a phenyl substituted with (Z)_(p1), or R²⁹ together with R²⁸ may form a C₂ to C₅ alkylene chain to form together with a nitrogen atom to which R²⁸ and R²⁹ are bonded, a 3- to 6-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom and may be optionally substituted with a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₆ alkoxy group, a —CHO group, a C₁ to C₆ alkylcarbonyl group, a C₁ to C₆ alkoxycarbonyl group, a phenyl group or a phenyl group substituted with (Z)_(p1),

R³⁰ represents a halogen atom, a cyano, a nitro, a C₃ to C₈ cycloalkyl, a C₃ to C₈ halocycloalkyl, E4, E5, E7, E8, E10, E12, E13, E15, E16, E18, a C₂ to C₆ alkenyl, a C₂ to C₆ haloalkenyl, a C₅ to C₈ cycloalkenyl, —OH, —OR³², —OC(O)R³¹, —OC(O)OR³², —OC(O)N(R³⁴)R³³, —OC(S)N(R³⁴)R³³, —SH, —S(O)_(r)R³², —S(═NR³³)R³², —S(R³²)═NC(O)R³¹, —S(O)(═NR³³)R³², —S(O)(R³²)═NC(O)R³¹, —SC(O)R³¹, —SC(O)OR³², —SC(O)N(R³⁴)R³³, —SC(S)N(R³⁴)R³³, —N(R³⁴)R³³, —N(R³⁴)C(O)R³¹, —N(R³⁴)C(O)OR³², —N(R³⁴)C(O)SR³², —N(R³⁴)C(O)N(R³⁴)R³³, —N(R³⁴)C(S)N(R³⁴)R³³, —N(R³⁴)S(O)₂R³², —C(O)R³¹, —C(O)OH, —C(O)OR³², —C(O)SR³², —C(O)N(R³⁴)R³³, —C(O)C(O)OR³², —P(O)(OR²⁰)₂, —P(S)(OR²⁰)₂, —P(phenyl)₂, —P(O)(phenyl)₂, a phenyl, a phenyl substituted with (Z)_(p1) or D1 to D38,

R³¹ represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a (C₁ to C₄) alkyl optionally substituted with R³⁵, a C₃ to C₆ cycloalkyl, a C₃ to C₆ halocycloalkyl, E4, E5, E12, E13, a C₂ to C₈ alkenyl, a C₂ to C₈ haloalkenyl, a C₅ to C₁₀ cycloalkenyl, a C₅ to C₁₀ halocycloalkenyl, a C₂ to C₈ alkynyl, a C₂ to C₈ haloalkynyl, a phenyl, a phenyl substituted with (Z)_(p1) or D1 to D38,

R³² represents a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a (C₁ to C₄) alkyl optionally substituted with R³⁵, a (C₁ to C₄) haloalkyl optionally substituted with R³⁵, a C₃ to C₆ cycloalkyl, E4, E5, a C₂ to C₈ alkenyl, a C₂ to C₈ haloalkenyl, a C₃ to C₈ alkynyl, a C₃ to C₈ haloalkynyl, a phenyl, a phenyl substituted with (Z)_(p1), D12, D32 or D34,

R³³ represents a hydrogen atom, a cyano, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a (C₁ to C₄) alkyl optionally substituted with R³⁵, a C₃ to C₆ cycloalkyl, E4, E5, E12, a C₂ to C₈ alkenyl, a C₂ to C₈ haloalkenyl, a C₃ to C₈ alkynyl, a phenyl, a phenyl substituted with (Z)_(p1), D1 to D25 or D27 to D38,

R³⁴ represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a cyano(C₁ to C₆) alkyl, a C₃ to C₆ cycloalkyl(C₁ to C₄) alkyl, a C₃ to C₈ cycloalkyl, a C₃ to C₆ alkenyl or a C₃ to C₆ alkynyl, or R³⁴ together with R³³ may form a C₂ to C₅ alkylene chain to form together with a nitrogen atom to which R³³ and R³⁴ are bonded, a 3- to 6-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom and may be optionally substituted with a halogen atom, a C₁ to C₄ alkyl group, a C₁ to C₄ alkoxy group, a —CHO group, a C₁ to C₄ alkylcarbonyl group, a C₁ to C₄ alkoxycarbonyl group, a phenyl group or a phenyl group substituted with (Z)_(p1),

R³⁵ represents a cyano, a C₃ to C₆ cycloalkyl, a C₃ to C₆ halocycloalkyl, E4, E5, E12, E13, a C₁ to C₄ alkoxy, a C₁ to C₄ haloalkoxy, a phenoxy, a phenoxy substituted with (Z)_(p1), a C₁ to C₄ alkylthio, a C₁ to C₄ haloalkylthio, a phenylthio, a phenylthio substituted with (Z)_(p1), a C₁ to C₄ alkylsulfonyl, a C₁ to C₄ haloalkylsulfonyl, a phenylsulfonyl, a phenylsulfonyl substituted with (Z)_(p1), —N(R³⁷)R³⁶, a C₁ to C₆ alkylcarbonyl, a C₁ to C₆ haloalkylcarbonyl, a C₁ to C₆ alkoxycarbonyl, a C₁ to C₆ alkylaminocarbonyl, a di(C₁ to C₆ alkyl)aminocarbonyl, a tri(C₁ to C₄ alkyl) silyl, a phenyl, a phenyl substituted with (Z)_(p1), a naphthyl or D1 to D38,

R³⁶ represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ alkylcarbonyl, a C₁ to C₆ haloalkylcarbonyl, a C₁ to C₆ alkoxycarbonyl, a phenylcarbonyl or a phenylcarbonyl substituted with (Z)_(p1),

R³⁷ represents a hydrogen atom or a C₁ to C₆ alkyl,

m represents an integer of 0 to 5,

n represents an integer of 0 to 4,

p represents an integer of 0 to 4,

p1 represents an integer of 1 to 5,

q represents an integer of 0 to 8,

r represents an integer of 0 to 2, and

t represents an integer of 0 or 1), and

a salt of the substituted isoxazoline compound or a salt of the substituted enone oxime compound.

[2] The substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound according to [1], in which

X represents a halogen atom, a cyano, a nitro, —SF₅, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a hydroxy(C₁ to C₄) haloalkyl, a C₁ to C₄ alkoxy(C₁ to C₄) haloalkyl, —OR⁵ or —S(O)_(r)R⁵, where when m represents an integer of 2 or more, Xs may be the same as or different from each other,

Y represents a halogen atom, a cyano, a nitro, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a (C₁ to C₄) alkyl optionally substituted with R⁴, a C₂ to C₆ alkenyl, a C₂ to C₆ alkynyl, —OR⁵, —S(O)_(r)R⁵, —NH₂, —N(R⁷)R⁶, —C(S)NH₂, D1 to D3, D7, D11 or D22, where when n represents an integer of 2 or more, Ys may be the same as or different from each other,

Z^(a) represents a halogen atom, a cyano, a nitro, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₁ to C₆ alkoxy, a C₁ to C₆ haloalkoxy, a C₁ to C₆ alkylthio, a C₁ to C₆ haloalkylthio, a C₁ to C₆ alkylsulfinyl, a C₁ to C₆ haloalkylsulfinyl, a C₁ to C₆ alkylsulfonyl, a C₁ to C₆ haloalkylsulfonyl, —NH₂, —C(O)N(R²)R¹ or —C(S)N(R²)R¹, where when p represents an integer of 2 or more, Z^(a)s may be the same as or different from each other,

R³ represents a C₁ to C₆ haloalkyl or a C₃ to C₈ halocycloalkyl,

R^(3a) represents a halogen atom, a C₁ to C₆ alkyl or a C₁ to C₆ alkylthio,

R^(3b) represents a hydrogen atom or a halogen atom,

R^(3c) represents a hydrogen atom, a halogen atom or a C₁ to C₆ alkyl,

R⁴ represents —OH, a C₁ to C₄ alkoxy, a C₁ to C₄ haloalkoxy, a C₁ to C₄ alkylthio, a C₁ to C₄ haloalkylthio, a C₁ to C₄ alkylsulfinyl, a C₁ to C₄ haloalkylsulfinyl, a C₁ to C₄ alkylsulfonyl or a C₁ to C₄ haloalkylsulfonyl,

R⁵ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl or a C₁ to C₂ haloalkoxy(C₁ to C₂) haloalkyl,

R⁶ represents a C₁ to C₄ alkyl, —C(O)R⁸, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹, —C(S)SR⁹ or —S(O)₂R⁹,

R⁷ represents a hydrogen atom or a C₁ to C₄ alkyl,

R⁸ represents a hydrogen atom, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl or a C₃ to C₆ cycloalkyl, and

R⁹ represents a C₁ to C₄ alkyl or a C₁ to C₄ haloalkyl.

[3] The substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound according to [2], in which

A¹ represents a carbon atom or a nitrogen atom,

A², A³ and A⁴ individually represent a carbon atom,

G¹ represents a benzene ring,

G² represents a structure represented by G²-1, G²-2, G²-4, G²-6, G²-7, G²-9 or G²-10,

L represents —C(R^(4a))(R^(4b))—,

X represents a halogen atom, a cyano, a nitro, —SF₅, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₁ to C₄ alkoxy, a C₁ to C₄ haloalkoxy, a C₁ to C₄ alkylthio or a C₁ to C₄ haloalkylthio, where when m represents 2 or 3, Xs may be the same as or different from each other,

Y represents a halogen atom, a cyano, a nitro, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₁ to C₂ alkoxy(C₁ to C₂) alkyl, a C₂ to C₄ alkynyl, a C₁ to C₄ alkoxy, a C₁ to C₄ haloalkoxy, a C₁ to C₄ alkylthio, a C₁ to C₄ haloalkylthio, —N(R⁷)R⁶ or —C(S)NH₂,

Z^(a) represents a halogen atom, a cyano, a nitro, a C₁ to C₄ alkyl, —NH₂, —C(O)N(R²)R¹ or —C(S)N(R²)R¹, where when p represents an integer of 2 or more, Z^(a)s may be the same as or different from each other,

R¹ represents a hydrogen atom, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R¹³, a C₃ to C₆ cycloalkyl, a (C₃ to C₆) cycloalkyl optionally substituted with R¹³, E4, E5, E12, a C₃ to C₆ alkenyl, a C₃ to C₆ haloalkenyl, a C₃ to C₆ alkynyl, a C₁ to C₆ alkylcarbonyl, —CH═NOR¹⁵, —C(O)OR¹⁵, —C(O)N(R¹⁷)R¹⁶, —C(S)OR¹⁵, —C(S)N(R¹⁷)R¹⁶, —C(OR¹⁵)═NOR¹⁵, —C(NH₂)═NCN, —C(NH₂)═NOR¹⁵, —C(NH₂)═NNO₂, —N(R¹⁷)R¹⁶, a phenyl substituted with (Z)_(p1), D1, D5 to D8, D10, D17 or D32 to D35,

R² represents a hydrogen atom, a C₁ to C₆ alkyl, a (C₁ to C₄) alkyl substituted with R^(13a), a C₃ to C₆ cycloalkyl, a C₃ to C₆ alkenyl, a C₃ to C₆ alkynyl, —C(O)R^(14a), —C(O)OR^(15a), —C(O)C(O)OR^(15a) or a C₁ to C₆ haloalkylthio, or R² together with R¹ may form ═C(R^(2b))R^(1b),

R^(1a) represents —C(O)R¹⁴, —C(O)OR¹⁵, —C(O)SR¹⁵, —C(O)N(R¹⁷)R¹⁶, —C(O)N(R¹⁷)N(R¹⁷)R¹⁶ or —C(S)R¹⁴,

R^(2a) represents a hydrogen atom, a C₁ to C₆ alkyl, a (C₁ to C₄) alkyl substituted with R^(13a), a C₃ to C₆ alkenyl or a C₃ to C₆ alkynyl,

R^(1b) represents a C₁ to C₆ alkyl, a C₁ to C₆ alkoxy, a C₁ to C₆ haloalkoxy, a C₁ to C₆ alkylthio or —N(R^(17b))R^(16b),

R^(2b) represents a C₁ to C₆ alkylthio or —N(R^(17c))R^(16c), or R^(2b) together with R^(1b) may form —N(R^(17c))CH═CHS— to form together with a carbon atom to which R^(1b) and R^(2b) are bonded, a 5-membered ring,

R³ represents a C₁ to C₄ haloalkyl,

R^(3a) represents a halogen atom or a C₁ to C₂ alkyl,

R^(3b) represents a hydrogen atom,

R^(3c) represents a hydrogen atom, a halogen atom or a C₁ to C₂ alkyl,

Z represents a halogen atom, a cyano, a nitro, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₁ to C₄ alkoxy, a C₁ to C₄ alkylsulfonyloxy or a C₁ to C₄ alkylthio, where when p and p1 individually represent an integer of 2 or more, Zs may be the same as or different from each other,

R^(4a) represents a hydrogen atom, a cyano, a C₁ to C₂ alkyl, a C₁ to C₂ haloalkyl, a C₂ to C₄ alkynyl or —C(S)NH₂,

R^(4b) represents a hydrogen atom,

R⁶ represents a hydrogen atom, a C₁ to C₄ alkyl, —CHO, a C₁ to C₄ alkylcarbonyl, a C₁ to C₄ haloalkylcarbonyl, a C₁ to C₄ alkoxycarbonyl, a C₁ to C₄ alkylthiocarbonyl, a C₁ to C₄ alkoxythiocarbonyl or a C₁ to C₄ alkyldithiocarbonyl,

R⁷ represents a hydrogen atom or a C₁ to C₄ alkyl,

R¹² represents a C₁ to C₄ alkyl,

R¹³ represents a halogen atom, a cyano, a C₃ to C₄ cycloalkyl, E4, E7, —OR²⁴, —N(R²⁵)R²⁴, —S(O)_(r)R²⁶, a C₁ to C₄ alkylcarbonyl, —C(R²⁷)═NOR²⁸, —C(O)N(R²⁹)R²⁸, —C(S)NH₂, a phenyl, a phenyl substituted with (Z)_(p1), D1, D5, D7, D8, D10, D13, D16, D17, D22, D32 or D34,

R^(13a) represents a cyano, a C₃ to C₄ cycloalkyl, —OR²⁴, —S(O)_(r)R²⁶, a C₁ to C₄ alkoxycarbonyl or D32,

R¹⁴ represents a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R³⁰, a C₃ to C₆ cycloalkyl, E4, E5, E10, a C₂ to C₆ alkenyl, a C₂ to C₆ haloalkenyl, a C₂ to C₆ alkynyl, a phenyl substituted with (Z)_(p1) or D32,

R^(14a) represents a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₁ to C₄ alkoxy(C₁ to C₄) alkyl, a C₁ to C₄ alkylthio(C₁ to C₄) alkyl, a C₁ to C₄ alkylsulfinyl(C₁ to C₄) alkyl, a C₁ to C₄ alkylsulfonyl(C₁ to C₄) alkyl, a C₃ to C₆ cycloalkyl, a C₂ to C₆ alkenyl, a C₂ to C₆ alkynyl, a phenyl, a phenyl substituted with (Z)_(p1) or D32,

R¹⁵ represents a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₃ to C₄ cycloalkyl(C₁ to C₄) alkyl, a C₁ to C₄ alkoxycarbonyl(C₁ to C₄) alkyl or a C₃ to C₆ alkenyl,

R^(15a) represents a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₁ to C₄ alkoxy(C₁ to C₄) alkyl, a C₃ to C₆ alkenyl, a C₃ to C₆ alkynyl or a phenyl,

R¹⁶ represents a hydrogen atom, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R³⁰, a C₃ to C₆ cycloalkyl, a C₃ to C₆ alkenyl, a C₃ to C₆ alkynyl, a C₁ to C₆ alkylcarbonyl, a C₁ to C₆ haloalkylcarbonyl, a C₁ to C₆ alkoxycarbonyl, a phenyl, a phenyl substituted with (Z)_(p1), D32 or D34,

R¹⁷ represents a hydrogen atom, a C₁ to C₆ alkyl, a C₃ to C₆ alkenyl or a C₃ to C₆ alkynyl, or R¹⁷ together with R¹⁶ may form a C₃ to C₅ alkylene chain to form together with a nitrogen atom to which R¹⁶ and R¹⁷ are bonded, a 4- to 6-membered ring, and in this case, the alkylene chain may contain one sulfur atom,

R^(16b) represents a cyano, a nitro or a C₁ to C₆ alkoxy,

R^(17b) represents a hydrogen atom or a C₁ to C₆ alkyl,

R^(16c) represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl or a C₁ to C₆ alkoxy,

R^(17c) represents a hydrogen atom or a C₁ to C₆ alkyl,

R²¹ represents a C₁ to C₂ alkyl,

R²⁴ represents a hydrogen atom, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, —C(O)R³¹ or —C(O)OR³²,

R²⁵ represents a hydrogen atom or a C₁ to C₄ haloalkyl,

R²⁶ represents a C₁ to C₄ alkyl,

R²⁷ represents a hydrogen atom or a C₁ to C₄ alkyl,

R²⁸ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a hydroxy(C₁ to C₄) haloalkyl, a C₃ to C₄ cycloalkyl, a C₃ to C₄ alkenyl or a C₃ to C₄ alkynyl,

R²⁹ represents a hydrogen atom or a C₁ to C₄ alkyl,

R³⁰ represents a halogen atom, a C₃ to C₆ cycloalkyl, a C₁ to C₄ alkoxy, a C₁ to C₄ haloalkoxy, —S(O)_(r)R³², —S(R³²)═NC(O)R³¹, —S(O)(R³²)═NH, —N(R³⁴)R³³, —N(R³⁴)C(O)R³¹, —N(R³⁴)C(O)OR³², —C(O)N(R³⁴)R³³, a phenyl substituted with (Z)_(p1) or D32,

R³¹ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl or a C₃ to C₆ cycloalkyl,

R³² represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl or a cyano(C₁ to C₂) alkyl,

R³³ represents a hydrogen atom, a C₁ to C₄ alkyl or a cyano(C₁ to C₂) alkyl,

R³⁴ represents a hydrogen atom or a cyano(C₁ to C₂) alkyl,

m represents an integer of 1 to 3,

n represents an integer of 0 or 1,

p represents an integer of 0 to 2, p1 represents an integer of 1 to 3,

q represents an integer of 0 or 1, and

t represents 0.

[4] The substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound according to [3], in which

G² represents a structure represented by G²-1, G²-2, G²-7 or G²-10,

X represents a halogen atom, a cyano, —SF₅, a C₁ to C₂ haloalkyl, a C₁ to C₂ haloalkoxy or a C₁ to C₂ haloalkylthio, where when m represents 2 or 3, Xs may be the same as or different from each other,

Y represents a halogen atom, a cyano, a nitro, a C₁ to C₂ alkyl, a C₁ to C₂ haloalkyl, a C₁ to C₂ alkoxymethyl, a C₂ to C₃ alkynyl, a C₁ to C₂ haloalkoxy, a C₁ to C₂ haloalkylthio, —N(R⁷)R⁶ or —C(S)NH₂,

Z^(a) represents a halogen atom, a nitro, a methyl or —NH₂,

R¹ represents a C₁ to C₄ alkyl, a (C₁ to C₄) alkyl optionally substituted with R¹³, a C₃ to C₄ cycloalkyl, a cyclopropyl substituted with R¹³, E4, E5, a C₃ to C₄ alkenyl, a C₃ to C₄ haloalkenyl, —CH═NOR¹⁵, —C(O)OR¹⁵, —C(O)NHR¹⁶, —C(S)OR¹⁵, —N(R¹⁷)R¹⁶, D34 or D35,

R² represents a hydrogen atom, a C₁ to C₄ alkyl, a (C₁ to C₂) alkyl substituted with R^(13a), a C₃ to C₄ alkynyl, —C(O)R^(14a), —C(O)OR^(15a) or a C₁ to C₄ haloalkylthio, or R² together with R¹ may form ═C(R^(2b))R^(1b),

R^(1a) represents —C(O)R¹⁴, —C(O)N(R¹⁷)R¹⁶ or —C(S)R¹⁴,

R^(2a) represents a hydrogen atom, a C₁ to C₄ alkyl, a (C₁ to C₂) alkyl substituted with R^(13a), a C₃ to C₄ alkenyl or a C₃ to C₄ alkynyl,

R^(1b) represents a C₁ to C₄ alkoxy or a C₁ to C₄ alkylthio,

R^(2b) represents —NHR^(16c),

R³ represents a C₁ to C₂ haloalkyl,

R^(3a) represents a halogen atom or a methyl,

R^(3c) represents a hydrogen atom,

Z represents a halogen atom, a cyano or a nitro,

R^(4a) represents a hydrogen atom, a cyano, a methyl or —C(S)NH₂,

R⁶ represents a hydrogen atom, a C₁ to C₂ alkyl or a C₁ to C₂ alkylcarbonyl,

R⁷ represents a hydrogen atom or a C₁ to C₂ alkyl,

R¹³ represents a halogen atom, a cyano, a C₃ to C₄ cycloalkyl, E4, E7, —OR²⁴, —NHR²⁴, —C(R²⁷)═NOR²⁸, —C(O)N(R²⁹)R²⁸, a phenyl, a phenyl substituted with (Z)_(p1), D8, D10, D13, D16, D22, D32 or D34,

R¹² represents a methyl,

R^(13a) represents a cyano, a C₃ to C₄ cycloalkyl, —OR²⁴ or a C₁ to C₄ alkylthio,

R¹⁴ represents a C₁ to C₄ alkyl, a (C₁ to C₄) alkyl optionally substituted with R³⁰, a C₃ to C₄ cycloalkyl, E4, E5, a C₂ to C₄ alkenyl, a C₂ to C₄ alkynyl or a phenyl substituted with (Z)_(p1),

R^(14a) represents a C₁ to C₄ alkyl, a C₁ to C₂ alkoxy(C₁ to C₂) alkyl, a C₃ to C₄ cycloalkyl or a C₂ to C₄ alkenyl,

R¹⁵ represents a C₁ to C₄ alkyl,

R^(15a) represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl or a C₁ to C₂ alkoxy(C₁ to C₂) alkyl,

R¹⁶ represents a hydrogen atom, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₃ to C₄ cycloalkyl, a C₃ to C₄ alkynyl, a phenyl, D32 or D34,

R¹⁷ represents a hydrogen atom, a C₁ to C₄ alkyl, a C₃ to C₄ alkenyl or a C₃ to C₄ alkynyl,

R^(16c) represents a hydrogen atom or a C₁ to C₄ alkyl,

R²¹ represents a methyl,

R²⁴ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₁ to C₄ alkylcarbonyl or a C₁ to C₄ alkoxycarbonyl,

R²⁷ represents a hydrogen atom or a C₁ to C₂ alkyl,

R²⁸ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₃ to C₄ alkenyl or a C₃ to C₄ alkynyl,

R²⁹ represents a hydrogen atom or a C₁ to C₂ alkyl,

R³⁰ represents a halogen atom, a C₃ to C₄ cycloalkyl, —S(O)_(r)R³², —N(R³⁴)R³³ or —C(O)N(R³⁴)R³³,

R³² represents a C₁ to C₄ alkyl or a C₁ to C₄ haloalkyl,

R³³ represents a C₁ to C₄ alkyl or a cyano(C₁ to C₂) alkyl, and

R³⁴ represents a hydrogen atom.

[5] The substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound according to [4], in which

A¹ represents a carbon atom,

G² represents a structure represented by G²-1,

W represents an oxygen atom,

X represents a halogen atom or a trifluoromethyl, where when m represents 2 or 3, Xs may be the same as or different from each other,

Y represents a halogen atom, a methyl, an ethyl or a trifluoromethyl,

R¹ represents a (C₁ to C₂) alkyl substituted with R¹³, E4, —CH═NOR¹⁵, —C(O)OR¹⁵, —C(O)NH₂, —N(R¹⁷)R¹⁶, D34 or D35,

R² represents a hydrogen atom, a (C₁ to C₂) alkyl substituted with R^(13a), a C₁ to C₃ alkylcarbonyl, a cyclopropylcarbonyl or a C₁ to C₃ alkoxycarbonyl,

R³ represents a trifluoromethyl or a chlorodifluoromethyl,

Z represents a halogen atom or a cyano,

R¹³ represents a halogen atom, a C₁ to C₃ alkoxy, a C₁ to C₂ haloalkoxy, —C(O)NHR²⁸, D10 or D32,

R^(13a) represents —OR²⁴,

R¹⁵ represents a C₁ to C₂ alkyl,

R¹⁶ represents a phenyl or D34,

R¹⁷ represents a C₁ to C₂ alkyl,

R²⁴ represents a C₁ to C₂ alkyl or a C₁ to C₂ alkylcarbonyl,

R²⁸ represents a C₁ to C₂ haloalkyl,

p represents an integer of 0 or 1, and

q represents 0.

[6] The substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound according to [4], in which

A¹ represents a carbon atom,

G² represents a structure represented by G²-2,

X represents a halogen atom or a trifluoromethyl, where when m represents 2 or 3, Xs may be the same as or different from each other,

Y represents a halogen atom, a nitro or a methyl,

R^(1a) represents —C(O)R¹⁴ or —C(O)NHR¹⁶,

R^(2a) represents a hydrogen atom, a C₁ to C₂ alkyl, a (C₁ to C₂) alkyl substituted with R^(13a) or a propargyl,

R³ represents a trifluoromethyl or a chlorodifluoromethyl,

R^(4a) represents a hydrogen atom, a cyano or a methyl,

R^(13a) represents a cyano, a cyclopropyl or a C₁ to C₂ alkoxy,

R¹⁴ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a (C₁ to C₂) alkyl substituted with R³⁰, a C₃ to C₄ cycloalkyl or E4,

R¹⁶ represents a C₁ to C₂ alkyl, a cyclopropyl or a propargyl,

R³⁰ represents a cyclopropyl, a C₁ to C₂ alkylthio, a C₁ to C₂ alkylsulfinyl or a C₁ to C₂ alkylsulfonyl, and

q represents 0.

[7] The substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound according to [4], in which

A¹ represents a carbon atom,

G² represents a structure represented by G²-7 or G²-10,

X represents a halogen atom or a trifluoromethyl, where when m represents 2 or 3, Xs may be the same as or different from each other,

Y represents a cyano or a nitro,

R³ represents a trifluoromethyl or a chlorodifluoromethyl, and

p represents 0.

[8] A substituted isoxazoline compound or a substituted enone oxime compound represented by General Formula (3) or General Formula (4):

(where A¹ and A² independently represent a carbon atom or a nitrogen atom,

Q represents a halogen atom, a cyano, a nitro, —CH(R^(4a))—R^(a), —OH, a C₁ to C₄ alkoxy, a C₁ to C₄ haloalkoxy, a halosulfonyloxy, a C₁ to C₄ alkylsulfonyloxy, a C₁ to C₄ haloalkylsulfonyloxy, a phenylsulfonyloxy, a phenylsulfonyloxy substituted with (Z)_(p1), a C₁ to C₄ alkylthio, a C₁ to C₄ alkylsulfinyl, a C₁ to C₄ alkylsulfonyl, a C₁ to C₄ haloalkylthio, a C₁ to C₄ haloalkylsulfinyl, a C₁ to C₄ haloalkylsulfonyl, —NH₂ or —C(O)R^(b),

X¹ represents a halogen atom, —SF₅, a C₁ to C₄ haloalkyl, a C₁ to C₄ haloalkoxy or a C₁ to C₄ haloalkylthio,

X² represents a halogen atom, a cyano, a nitro, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₁ to C₄ alkoxy, a C₁ to C₄ haloalkoxy, a C₁ to C₄ alkylthio or a C₁ to C₄ haloalkylthio, where when m1 represents 2, X²s may be the same as or different from each other,

Y represents a halogen atom, a cyano, a nitro, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₁ to C₂ alkoxy(C₁ to C₂) alkyl, a C₂ to C₄ alkynyl, a C₁ to C₄ alkoxy, a C₁ to C₄ haloalkoxy, a C₁ to C₄ alkylthio, a C₁ to C₄ haloalkylthio, —N(R⁷)R⁶ or —C(S)NH₂,

Z represents a halogen atom or a methyl, where when p1 represents an integer of 2 or more, Zs may be the same as or different from each other,

R^(a) represents a hydrogen atom, a halogen atom, —OH, a C₁ to C₂ alkylcarbonyloxy, a C₁ to C₂ alkylsulfonyloxy, a C₁ to C₂ haloalkylsulfonyloxy or —NH₂,

R^(b) represents a hydrogen atom, a halogen atom, a C₁ to C₂ alkyl, a C₁ to C₂ haloalkyl, —OH, a C₁ to C₄ alkoxy, a 1-pyrazolyl, a 1-imidazolyl or a 1-triazolyl,

R³ represents a C₁ to C₄ haloalkyl,

R^(3a) represents a halogen atom or a C₁ to C₂ alkyl,

R^(3c) represents a hydrogen atom, a halogen atom or a C₁ to C₂ alkyl,

R^(4a) represents a hydrogen atom, a C₁ to C₂ alkyl or a C₁ to C₂ haloalkyl,

R⁶ represents a hydrogen atom, a C₁ to C₄ alkyl, —CHO, a C₁ to C₄ alkylcarbonyl, a C₁ to a C₄ haloalkylcarbonyl, a C₁ to C₄ alkoxycarbonyl, a C₁ to C₄ alkylthiocarbonyl, a C₁ to C₄ alkoxythiocarbonyl or a C₁ to C₄ alkyldithiocarbonyl,

R⁷ represents a hydrogen atom or a C₁ to C₄ alkyl,

m1 represents an integer of 0 to 2,

n represents an integer of 0 or 1, and

p1 represents an integer of 1 to 5), and

a salt of the substituted isoxazoline compound or a salt of the substituted enone oxime compound.

[9] The substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound according to [8], in which

Q represents a halogen atom, a cyano, a nitro, a C₁ to C₂ alkyl, a C₁ to C₂ haloalkyl, a hydroxy(C₁ to C₂) alkyl, —OH, a C₁ to C₂ alkoxy, a C₁ to C₂ haloalkoxy, a C₁ to C₂ alkylsulfonyloxy, a C₁ to C₂ haloalkylsulfonyloxy, a C₁ to C₂ alkylthio, a C₁ to C₂ alkylsulfinyl, a C₁ to C₂ alkylsulfonyl, —NH₂ or —C(O)R^(b),

X¹ represents a halogen atom, —SF₅, a C₁ to C₂ haloalkyl, a C₁ to C₂ haloalkoxy or a C₁ to C₂ haloalkylthio,

X² represents a halogen atom, a cyano, a C₁ to C₂ haloalkyl, a C₁ to C₂ haloalkoxy or a C₁ to C₂ haloalkylthio, where when m1 represents 2, X²s may be the same as or different from each other,

Y represents a halogen atom, a cyano, a nitro, a C₁ to C₂ alkyl, a C₁ to C₂ haloalkyl, a C₁ to C₂ alkoxymethyl, a C₂ to C₃ alkynyl, a C₁ to C₂ haloalkoxy, a C₁ to C₂ haloalkylthio, —N(R⁷)R⁶ or —C(S)NH₂,

R^(b) represents a hydrogen atom, a halogen atom, a methyl, —OH or a C₁ to C₂ alkoxy,

R³ represents a C₁ to C₂ haloalkyl,

R^(3a) represents a halogen atom or a methyl,

R⁶ represents a hydrogen atom, a C₁ to C₂ alkyl or a C₁ to C₂ alkylcarbonyl, and

R⁷ represents a hydrogen atom or a C₁ to C₂ alkyl.

[10] The substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound according to [9], in which

A¹ represents a carbon atom or a nitrogen atom,

A² represents a carbon atom,

Q represents a halogen atom, a cyano, a nitro, a methylthio, a methylsulfinyl or a methylsulfonyl,

X¹ and X² independently represent a halogen atom or a trifluoromethyl, where when m1 represents 2, X²s may be the same as or different from each other,

Y represents a halogen atom, a cyano, a nitro, a methyl, an ethyl or a trifluoromethyl,

R³ represents a trifluoromethyl or a chlorodifluoromethyl, and

R^(3a) represents a halogen atom or a methyl.

[11] A pest control agent containing one type or two or more types selected from the substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound as described in [1] to [10], as active ingredient(s). [12] An agricultural chemical containing one type or two or more types selected from the substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound as described in [1] to [10], as active ingredient(s). [13] A control agent against internal or external parasites of mammals or birds containing one type or two or more types selected from the substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound as described in [1] to [10], as active ingredient(s). [14] An insecticide or a miticide containing one type or two or more types selected from the substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound as described in [1] to [10], as active ingredient(s).

EFFECTS OF THE INVENTION

The compound of the present invention has excellent insecticidal and miticidal activity with respect to a number of agricultural insect pests, spider mites and internal or external parasites of mammals or birds, and also exerts satisfactory control effect on insect pests which have acquired resistance to related art pesticides. Furthermore, the compound has substantially no adverse effect on mammals, fish and beneficial insects, and has a low residual property to have a light burden on the environment.

Accordingly, the present invention can provide a useful novel pest control agent.

BEST MODES FOR CARRYING OUT THE INVENTION

In the compounds included in the present invention, although geometric isomers of an E-form and a Z-form may exist depending on a substituent type, the present invention includes the E-form, the Z-form or a mixture containing the E-form and the Z-form at any ratio. Furthermore, although the compounds included in the present invention include optically active substances due to the presence of one or more asymmetric carbon atom(s), the present invention includes all of the optically active compounds or racemic bodies.

Among the compounds included in the present invention, compounds capable of being converted into acid addition salts by a common method may be converted into, for example, salts of hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydriodic acid; salts of inorganic acids such as nitric acid, sulfuric acid, phosphoric acid, chloric acid and perchloric acid; salts of sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid; salts of carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid and citric acid; or salts of amino acids such as glutamic acid and aspartic acid.

In addition, among the compounds included in the present invention, compounds capable of being converted into metal salts by a common method may be converted into, for example, salts of alkali metals such as lithium, sodium and potassium; salts of alkaline earth metals such as calcium, barium and magnesium; or salts of aluminum.

Next, specific examples of each substituent shown in the present specification are shown below. Here, n-, s- and tert-mean normal, iso, secondary and tertiary, respectively, and Ph means phenyl.

Examples of halogen atoms in the compound of the present invention include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. Here, the expression “halo” in the present specification also represents these halogen atoms.

The expression “C_(a) to C_(b) alkyl” in the present specification represents a straight chain or branched chain hydrocarbon group having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) alkyl” include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, an s-butyl group, a tert-butyl group, an n-pentyl group, a 1,1-dimethylpropyl group and an n-hexyl group, and each of the alkyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) haloalkyl” in the present specification represents a straight chain or branched chain hydrocarbon group having a to b pieces of carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. In this case, when hydrogen atoms are substituted with two or more halogen atoms, these halogen atoms may be the same as or different from each other. Specific examples of the “C_(a) to C_(b) haloalkyl” include a fluoromethyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a trichloromethyl group, a bromodifluoromethyl group, a 2-fluoroethyl group, a 2-chloroethyl group, a 2-bromoethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 2-chloro-2,2-difluoroethyl group, a 2,2,2-trichloroethyl group, a 1,1,2,2-tetrafluoroethyl group, a 2-chloro-1,1,2-trifluoroethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a 1,1,2,3,3,3-hexafluoropropyl group, a heptafluoropropyl group, a 2,2,2-trifluoro-1-(trifluoromethyl)ethyl group, a 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group and a nonafluorobutyl group. Each of the haloalkyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) cycloalkyl” in the present specification represents a cyclic hydrocarbon group having a to b pieces of carbon atoms, and the “C_(a) to C_(b) cycloalkyl” can form a monocyclic or composite ring structure having a 3-membered ring to a 6-membered ring. Furthermore, each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms. Specific examples of the “C_(a) to C_(b) cycloalkyl” include a cyclopropyl group, a 1-methylcyclopropyl group, a 2-methylcyclopropyl group, a 2,2-dimethylcyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group, and each of the cycloalkyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) halocycloalkyl” in the present specification represents a cyclic hydrocarbon group having a to b pieces of carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom, and the “C_(a) to C_(b) halocycloalkyl” can form a monocyclic or composite ring structure having a 3-membered ring to a 6-membered ring. Furthermore, each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, the substitution of a halogen atom may be on the ring structure part, the side chain part or both of them. Furthermore, when hydrogen atoms are substituted with two or more halogen atoms, these halogen atoms may be the same as or different from each other. Specific examples of the “C_(a) to C_(b) halocycloalkyl” include a 2,2-difluorocyclopropyl group, a 2,2-dichlorocyclopropyl group, a 2,2-dibromocyclopropyl group, a 2,2-difluoro-1-methylcyclopropyl group, a 2,2-dichloro-1-methylcyclopropyl group, a 2,2-dibromo-1-methylcyclopropyl group and a 2,2,3,3-tetrafluorocyclobutyl group, and each of the halocycloalkyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) alkenyl” in the present specification represents a straight chain or branched chain unsaturated hydrocarbon group having a to b pieces of carbon atoms and one or more double bond(s) in the molecule. Specific examples of the “C_(a) to C_(b) alkenyl” include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methylethenyl group, a 2-butenyl group, a 2-methyl-2-propenyl group, a 3-methyl-2-butenyl group and a 1,1-dimethyl-2-propenyl group, and each of the alkenyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) haloalkenyl” in the present specification represents a straight chain or branched chain unsaturated hydrocarbon group having a to b pieces of carbon atoms and one or more double bond(s) in the molecule in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. In this case, when hydrogen atoms are substituted with two or more halogen atoms, these halogen atoms may be the same as or different from each other. Specific examples of the “C_(a) to C_(b) haloalkenyl” include a 2,2-dichlorovinyl group, a 2-fluoro-2-propenyl group, a 2-chloro-2-propenyl group, a 3-chloro-2-propenyl group, a 2-bromo-2-propenyl group, a 3,3-difluoro-2-propenyl group, a 2,3-dichloro-2-propenyl group, a 3,3-dichloro-2-propenyl group, a 2,3,3-trifluoro-2-propenyl group, a 2,3,3-trichloro-2-propenyl group, a 1-(trifluoromethyl)ethenyl group, a 4,4-difluoro-3-butenyl group, a 3,4,4-trifluoro-3-butenyl group and a 3-chloro-4,4,4-trifluoro-2-butenyl group, and each of the haloalkenyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) cycloalkenyl” in the present specification represents a cyclic unsaturated hydrocarbon group having a to b pieces of carbon atoms and one or more double bond(s), and the “C_(a) to C_(b) cycloalkenyl” can form a monocyclic or composite ring structure having a 3-membered ring to a 6-membered ring. Furthermore, each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, and moreover, the double bond may be either an endo- or exo-type. Specific examples of the “C_(a) to C_(b) cycloalkenyl group” include a 1-cyclopenten-1-yl group, a 2-cyclopenten-1-yl group, a 1-cyclohexen-1-yl group and a 2-cyclohexen-1-yl group, and each of the cycloalkenyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) halocycloalkenyl” in the present specification represents a cyclic unsaturated hydrocarbon group having a to b pieces of carbon atoms and one or more double bond(s) in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom, and the “C_(a) to C_(b) halocycloalkenyl” can form a monocyclic or composite ring structure having a 3-membered ring to a 6-membered ring. Furthermore, each ring may be optionally substituted with an alkyl group within the range of a specified number of carbon atoms, and moreover, the double bond may be either an endo- or exo-type. In addition, the substitution of a halogen atom may be on the ring structure part, the side chain part or both of them, and when hydrogen atoms are substituted with two or more halogen atoms, these halogen atoms may be the same as or different from each other. Specific examples of the “C_(a) to C_(b) halocycloalkenyl” include a 2-fluoro-1-cyclopentenyl group, a 2-chloro-1-cyclopentenyl group, a 3-chloro-2-cyclopentenyl group and a 2-fluoro-1-cyclohexenyl group, and each of the halocycloalkenyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) alkylidene” in the present specification represents a straight chain or branched chain hydrocarbon group having a to b pieces of carbon atoms and bonded through its double bond. Specific examples of the “C_(a) to C_(b) alkylidene” include a methylidene group, an ethylidene group, a propylidene group and a 1-methylethylidene group, and each of the alkylidene groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) haloalkylidene” in the present specification represents a straight chain or branched chain unsaturated hydrocarbon group having a to b pieces of carbon atoms and one or more double bond(s) in the molecule and bonded through the double bond(s), in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. In this case, when hydrogen atoms are substituted with two or more halogen atoms, these halogen atoms may be the same as or different from each other. Specific examples of the “C_(a) to C_(b), haloalkylidene” include a difluoromethylidene group, a dichloromethylidene group and a 2,2,2-trifluoroethylidene group, and each of the haloalkylidene groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) alkynyl” in the present specification represents a straight chain or branched chain unsaturated hydrocarbon group having a to b pieces of carbon atoms and one or more triple bond(s) in the molecule. Specific examples of the “C_(a) to C_(b) alkynyl” include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group and a 1,1-dimethyl-2-propynyl group, and each of the alkynyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) haloalkynyl” in the present specification represents a straight chain or branched chain unsaturated hydrocarbon group having a to b pieces of carbon atoms and one or more triple bond(s) in the molecule in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. In this case, when hydrogen atoms are substituted with two or more halogen atoms, these halogen atoms may be the same as or different from each other. Specific examples of the “C_(a) to C_(b), haloalkynyl” include a 2-chloroethynyl group, a 2-bromoethynyl group, a 2-iodoethynyl group, a 3-chloro-2-propynyl group, a 3-bromo-2-propynyl group and a 3-iodo-2-propynyl group, and each of the haloalkynyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b), alkoxy” in the present specification represents an alkyl-O— group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b), alkoxy” include a methoxy group, an ethoxy group, an n-propyloxy group, an i-propyloxy group, an n-butyloxy group, an i-butyloxy group, an s-butyloxy group and a tert-butyloxy group, and each of the alkoxy groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b), haloalkoxy” in the present specification represents a haloalkyl-O— group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) haloalkoxy” include a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoromethoxy group, a bromodifluoromethoxy group, a 2-fluoroethoxy group, a 2-chloroethoxy group, a 2,2,2-trifluoroethoxy group, a 1,1,2,2-tetrafluoroethoxy group, a 2-chloro-1,1,2-trifluoroethoxy group and a 1,1,2,3,3,3-hexafluoropropyloxy group, and each of the haloalkoxy groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) alkenyloxy” in the present specification represents an alkenyl-O— group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) alkenyloxy” include a 2-propenyloxy group, a 2-butenyloxy group, a 2-methyl-2-propenyloxy group and a 3-methyl-2-butenyloxy group, and each of the alkenyloxy groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) alkylthio” in the present specification represents an alkyl-S— group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) alkylthio” include a methylthio group, an ethylthio group, an n-propylthio group, an i-propylthio group, an n-butylthio group, an i-butylthio group, an s-butylthio group and a tert-butylthio group, and each of the alkylthio groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) haloalkylthio” in the present specification represents a haloalkyl-S— group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) haloalkylthio” include a difluoromethylthio group, a trifluoromethylthio group, a chlorodifluoromethylthio group, a bromodifluoromethylthio group, a 2,2,2-trifluoroethylthio group, a 1,1,2,2-tetrafluoroethylthio group, a 2-chloro-1,1,2-trifluoroethylthio group, a pentafluoroethylthio group, a 1,1,2,3,3,3-hexafluoropropylthio group, a heptafluoropropylthio group, a 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethylthio group and a nonafluorobutylthio group, and each of the haloalkylthio groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) alkylsulfinyl” in the present specification represents an alkyl-S(O)— group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) alkylsulfinyl” include a methylsulfinyl group, an ethylsulfinyl group, an n-propylsulfinyl group, an i-propylsulfinyl group, an n-butylsulfinyl group, an i-butylsulfinyl group, an s-butylsulfinyl group and a tert-butylsulfinyl group, and each of the alkylsulfinyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) haloalkylsulfinyl” in the present specification represents a haloalkyl-S(O)— group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) haloalkylsulfinyl” include a difluoromethylsulfinyl group, a trifluoromethylsulfinyl group, a chlorodifluoromethylsulfinyl group, a bromodifluoromethylsulfinyl group, a 2,2,2-trifluoroethylsulfinyl group, a 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethylsulfinyl group and a nonafluorobutylsulfinyl group, and each of the haloalkylsulfinyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) alkylsulfonyl” in the present specification represents an alkyl-SO₂— group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) alkylsulfonyl” include a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, an i-propylsulfonyl group, an n-butylsulfonyl group, an i-butylsulfonyl group, an s-butylsulfonyl group and a tert-butylsulfonyl group, and each of the alkylsulfonyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) haloalkylsulfonyl” in the present specification represents a haloalkyl-SO₂— group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) haloalkylsulfonyl” include a difluoromethylsulfonyl group, a trifluoromethylsulfonyl group, a chlorodifluoromethylsulfonyl group, a bromodifluoromethylsulfonyl group, a 2,2,2-trifluoroethylsulfonyl group, a 1,1,2,2-tetrafluoroethylsulfonyl group and a 2-chloro-1,1,2-trifluoroethylsulfonyl group, and each of the haloalkylsulfonyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) alkylamino” in the present specification represents an amino group in which one of the hydrogen atoms is substituted with an alkyl group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) alkylamino” include a methylamino group, an ethylamino group, an n-propylamino group, an i-propylamino group, an n-butylamino group, an i-butylamino group and a tert-butylamino group, and each of the alkylamino groups is selected from within the range of the specified number of carbon atoms.

The expression “di(C_(a) to C_(b) alkyl)amino” in the present specification represents an amino group in which both of the hydrogen atoms are substituted with alkyl groups as defined above having a to b pieces of carbon atoms and the alkyl groups may be the same as or different from each other. Specific examples of the “di(C_(a) to C_(b) alkyl)amino” include a dimethylamino group, an ethyl(methyl)amino group, a diethylamino group, an n-propyl(methyl)amino group, an i-propyl(methyl)amino group, a di(n-propyl)amino group and a di(n-butyl)amino group, and each of the dialkylamino groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) alkylimino” in the present specification represents an alkyl-N═ group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) alkylimino” include a methylimino group, an ethylimino group, an n-propylimino group, an i-propylimino group, an n-butylimino group, an i-butylimino group and an s-butylimino group, and each of the alkylimino groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) alkoxyimino” in the present specification represents an alkoxy-N═ group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) alkoxyimino” include a methoxyimino group, an ethoxyimino group, an n-propyloxyimino group, an i-propyloxyimino group and an n-butyloxyimino group, and each of the alkoxyimino groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) alkylcarbonyl” in the present specification represents an alkyl-C(O)— group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) alkylcarbonyl” include an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a valeryl group, an isovaleryl group, a 2-methylbutanoyl group, a pivaloyl group, a hexanoyl group and a heptanoyl group, and each of the alkylcarbonyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) haloalkylcarbonyl” in the present specification represents a haloalkyl-C(O)— group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) haloalkylcarbonyl” include a fluoroacetyl group, a chloroacetyl group, a difluoroacetyl group, a dichloroacetyl group, a trifluoroacetyl group, a chlorodifluoroacetyl group, a bromodifluoroacetyl group, a trichloroacetyl group, a pentafluoropropionyl group, a heptafluorobutanoyl group and a 3-chloro-2,2-dimethylpropanoyl group, and each of the haloalkylcarbonyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) cycloalkylcarbonyl” in the present specification represents a cycloalkyl-C(O)— group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) cycloalkylcarbonyl” include a cyclopropylcarbonyl group, a 2-methylcyclopropylcarbonyl group and a cyclobutylcarbonyl group, and each of the cycloalkylcarbonyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) halocycloalkylcarbonyl” in the present specification represents a halocycloalkyl-C(O)— group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) halocycloalkylcarbonyl” include a 2,2-dichlorocyclopropylcarbonyl group and a 2,2-dichloro-1-methylcyclopropylcarbonyl group, and each of the halocycloalkylcarbonyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) alkoxycarbonyl” in the present specification represents an alkyl-O—C(O)— group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) alkoxycarbonyl” include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propyloxycarbonyl group, an i-propyloxycarbonyl group, an n-butoxycarbonyl group, an i-butoxycarbonyl group and a tert-butoxycarbonyl group, and each of the alkoxycarbonyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) haloalkoxycarbonyl” in the present specification represents a haloalkyl-O—C(O)— group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) haloalkoxycarbonyl” include a chloromethoxycarbonyl group, a 2-chloroethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, a 2,2,2-trifluoroethoxycarbonyl group and a 2,2,2-trichloroethoxycarbonyl group, and each of the haloalkoxycarbonyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) alkylthiocarbonyl” in the present specification represents an alkyl-S—C(O)— group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) alkylthiocarbonyl” include a methylthio-C(O)— group, an ethylthio-C(O)— group, an n-propylthio-C(O)— group, an i-propylthio-C(O)— group, an n-butylthio-C(O)— group, an i-butylthio-C(O)— group and a tert-butylthio-C(O)— group, and each of the alkylthiocarbonyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) alkoxythiocarbonyl” in the present specification represents an alkyl-O—C(S)— group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) alkoxythiocarbonyl” include a methoxy-C(S)— group, an ethoxy-C(S)— group, an n-propyloxy-C(S)— group and an i-propyloxy-C(S)— group, and each of the alkoxythiocarbonyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) alkyldithiocarbonyl” in the present specification represents an alkyl-S—C(S)— group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b), alkyldithiocarbonyl” include a methylthio-C(S)— group, an ethylthio-C(S)— group, an n-propylthio-C(S)— group and an i-propylthio-C(S)— group, and each of the alkyldithiocarbonyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) alkylaminocarbonyl” in the present specification represents a carbamoyl group in which one of the hydrogen atoms is substituted with an alkyl group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b), alkylaminocarbonyl” include a methylcarbamoyl group, an ethylcarbamoyl group, an n-propylcarbamoyl group, an i-propylcarbamoyl group, an n-butylcarbamoyl group, an i-butylcarbamoyl group, an s-butylcarbamoyl group and a tert-butylcarbamoyl group, and each of the alkylaminocarbonyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) haloalkylaminocarbonyl” in the present specification represents a carbamoyl group in which one of the hydrogen atoms is substituted with a haloalkyl group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) haloalkylaminocarbonyl” include a 2-fluoroethylcarbamoyl group, a 2-chloroethylcarbamoyl group, a 2,2-difluoroethylcarbamoyl group and a 2,2,2-trifluoroethylcarbamoyl group, and each of the haloalkylaminocarbonyl groups is selected from within the range of the specified number of carbon atoms.

The expression “di(C_(a) to C_(b) alkyl)aminocarbonyl” in the present specification represents a carbamoyl group in which both of the hydrogen atoms are substituted with alkyl groups as defined above having a to b pieces of carbon atoms and the alkyl groups may be the same as or different from each other. Specific examples of the “di(C_(a) to C_(b) alkyl)aminocarbonyl” include an N,N-dimethylcarbamoyl group, an N-ethyl-N-methylcarbamoyl group, an N,N-diethylcarbamoyl group, an N,N-di(n-propyl)carbamoyl group and an N,N-di(n-butyl)carbamoyl group, and each of the dialkylaminocarbonyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) alkylaminosulfonyl” in the present specification represents a sulfamoyl group in which one of the hydrogen atoms is substituted with an alkyl group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) alkylaminosulfonyl” include a methylsulfamoyl group, an ethylsulfamoyl group, an n-propylsulfamoyl group, an i-propylsulfamoyl group, an n-butylsulfamoyl group, an i-butylsulfamoyl group, an s-butylsulfamoyl group and a tert-butylsulfamoyl group, and each of the alkylaminosulfonyl groups is selected from within the range of the specified number of carbon atoms.

The expression “di(C_(a) to C_(b) alkyl)aminosulfonyl” in the present specification represents a sulfamoyl group in which both of the hydrogen atoms are substituted with alkyl groups as defined above having a to b pieces of carbon atoms and the alkyl groups may be the same as or different from each other. Specific examples of the “di(C_(a) to C_(b), alkyl)aminosulfonyl” include an N,N-dimethylsulfamoyl group, an N-ethyl-N-methylsulfamoyl group, an N,N-diethylsulfamoyl group, an N,N-di(n-propyl)sulfamoyl group and an N,N-di(n-butyl)sulfamoyl group, and each of the dialkylaminosulfonyl groups is selected from within the range of the specified number of carbon atoms.

The expression “tri(C_(a) to C_(b) alkyl)silyl” in the present specification represents a silyl group which is substituted with alkyl groups as defined above having a to b pieces of carbon atoms and the alkyl groups may be the same as or different from each other. Specific examples of the “tri(C_(a) to C_(b) alkyl)silyl” include a trimethylsilyl group, a triethylsilyl group, a tri(n-propyl)silyl group, an ethyldimethylsilyl group, an n-propyldimethylsilyl group, an n-butyldimethylsilyl group, an i-butyldimethylsilyl group and a tert-butyldimethylsilyl group, and each of the trialkylsilyl groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) alkylcarbonyloxy” in the present specification represents an alkylcarbonyl-O— group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) alkylcarbonyloxy” include an acetoxy group, and each of the alkylcarbonyloxy groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) alkylsulfonyloxy” in the present specification represents an alkylsulfonyl-O— group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b) alkylsulfonyloxy” include a methylsulfonyloxy group, an ethylsulfonyloxy group, an n-propylsulfonyloxy group and an i-propylsulfonyloxy group, and each of the alkylsulfonyloxy groups is selected from within the range of the specified number of carbon atoms.

The expression “C_(a) to C_(b) haloalkylsulfonyloxy” in the present specification represents a haloalkylsulfonyl-O— group as defined above having a to b pieces of carbon atoms. Specific examples of the “C_(a) to C_(b), haloalkylsulfonyloxy” include a difluoromethylsulfonyloxy group, a trifluoromethylsulfonyloxy group, a chlorodifluoromethylsulfonyloxy group and a bromodifluoromethylsulfonyloxy group, and each of the haloalkylsulfonyloxy groups is selected from within the range of the specified number of carbon atoms.

Each expression “C_(a) to C_(b) cycloalkyl(C_(d) to C_(e)) alkyl”, “hydroxy(C_(d) to C_(e)) alkyl”, “C_(a) to C_(b) alkoxy(C_(d) to C_(e)) alkyl”, “C_(a) to C_(b) haloalkoxy(C_(d) to C_(e)) alkyl”, “C_(a) to C_(b) alkylthio(C_(d) to C_(e)) alkyl”, “C_(a) to C_(b) haloalkylthio(C_(d) to C_(e)) alkyl”, “C_(a) to C_(b) alkylsulfinyl(C_(d) to C_(e)) alkyl”, “C_(a) to C_(b) haloalkylsulfinyl(C_(d) to C_(e)) alkyl”, “C_(a) to C_(b) alkylsulfonyl(C_(d) to C_(e)) alkyl”, “C_(a) to C_(b) haloalkylsulfonyl(C_(d) to C_(e))alkyl”, “cyano(C_(d) to C_(e)) alkyl”, “C_(a) to C_(b) alkoxycarbonyl(C_(d) to C_(e)) alkyl”, “C_(a) to C_(b) haloalkoxycarbonyl(C_(d) to C_(e)) alkyl”, “phenyl(C_(d) to C_(e)) alkyl”, “phenyl(C_(d) to C_(e)) alkyl substituted with (Z)_(p1)” or the like in the present specification represents an alkyl group as defined above having d to e pieces of carbon atoms in which a hydrogen atom bonded to a carbon atom is substituted with any of a C_(a) to C_(b) cycloalkyl group, a C_(a) to C_(b) alkoxy group, a C_(a) to C_(b) haloalkoxy group, a C_(a) to C_(b) alkylthio group, a C_(a) to C_(b) haloalkylthio group, a C_(a) to C_(b) alkylsulfinyl group, a C_(a) to C_(b) haloalkylsulfinyl group, a C_(a) to C_(b) alkylsulfonyl group, a C_(a) to C_(b) haloalkylsulfonyl group, a C_(a) to C_(b) alkoxycarbonyl group, a C_(a) to C_(b) haloalkoxycarbonyl group, a hydroxy group, a cyano group, a phenyl group or a phenyl group substituted with (Z)_(p1), all of which are as defined above. Each of the alkyl groups is selected from within the range of the specified number of carbon atoms.

Each expression “(C_(a) to C_(b)) alkyl optionally substituted with R⁴”, “(C_(a) to C_(b)) alkyl optionally substituted with R¹³”, “(C_(a) to C_(b)) alkyl optionally substituted with R^(13a)”, “(C_(a) to C_(b)) alkyl optionally substituted with R²³”, “(C_(a) to C_(b)) alkyl optionally substituted with R³⁰”, “(C_(a) to C_(b)) alkyl optionally substituted with R³⁵” or the like in the present specification represents an alkyl group as defined above having a to b pieces of carbon atoms in which a hydrogen atom bonded to a carbon atom is Each of the alkyl groups is selected from within the range of the specified number of carbon atoms. In this case, when the number of substituents R⁴, R¹³, R^(13a), R²³, R³⁰ or R³⁵ on each (C_(a) to C_(b)) alkyl group is two or more, R⁴, R¹³, R^(13a), R²³, R³⁰s or R³⁵s may be the same as or different from each other.

Each expression “hydroxy(C_(d) to C_(e)) haloalkyl, “C_(a) to C_(b) alkoxy(C_(d) to C_(e)) haloalkyl” or “C_(a) to C_(b) haloalkoxy(C_(d) to C_(e)) haloalkyl” in the present specification represents a haloalkyl group as defined above having d to e pieces of carbon atoms in which a hydrogen atom or a halogen atom bonded to a carbon atom is substituted with any of a C_(a) to C_(b) alkoxy group, a C_(a) to C_(b) haloalkoxy group or a hydroxy group, all of which are as defined above. Each of the haloalkyl groups is selected from within the range of the specified number of carbon atoms.

The expression “(C_(a) to C_(b)) haloalkyl optionally substituted with R³⁵” in the present specification represents a haloalkyl group as defined above having a to b pieces of carbon atoms in which a hydrogen atom or a halogen atom bonded to a carbon atom is optionally substituted with any of R³⁵, and each of the haloalkyl groups is selected from within the range of the specified number of carbon atoms. In this case, when the number of substituents R³⁵ on the (C_(a) to C_(b)) haloalkyl group is two or more, R³⁵s may be the same as or different from each other.

Each expression “hydroxy(C_(d) to C_(a)) cycloalkyl”, “C_(a) to C_(b) alkoxy(C_(d) to C_(e)) cycloalkyl” or the like in the present specification represents a cycloalkyl group as defined above having d to e pieces of carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with any of a C_(a) to C_(b) alkoxy group or a hydroxy group, both of which are as defined above, and each of the cycloalkyl groups is selected from within the range of the specified number of carbon atoms.

Each expression “(C_(a) to C_(b)) cycloalkyl optionally substituted with R⁴”, “(C_(a) to C_(b)) cycloalkyl optionally substituted with R¹³”, “(C_(a) to C_(b)) cycloalkyl optionally substituted with R²³”, “(C_(a) to C_(b)) cycloalkyl optionally substituted with R³⁰” or the like in the present specification represents a cycloalkyl group as defined above having a to b pieces of carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with any of R⁴, R¹³, R²³ or R³⁰, and each of the cycloalkyl groups is selected from within the range of the specified number of carbon atoms. In this case, the substitution of R⁴, R¹³, R²³ or R³⁰ may be on the ring structure part, the side chain part or both of them. Furthermore, when the number of substituents R⁴, R¹³, R²³ or R³⁰ on each (C_(a) to C_(b)) cycloalkyl group is two or more, R⁴s, R¹³s, R²³s or R³⁰s may be the same as or different from each other.

The expression “phenyl(C_(a) to C_(b)) alkenyl” in the present specification represents an alkenyl group as defined above having a to b pieces of carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a phenyl group, and each of the alkenyl groups is selected from within the range of the specified number of carbon atoms.

Each expression “(C_(a) to C_(b)) alkenyl optionally substituted with R⁴”, “(C_(a) to C_(b)) alkenyl optionally substituted with R¹³”, “(C_(a) to C_(b)) alkenyl optionally substituted with R²³” or “(C_(a) to C_(b)) alkenyl optionally substituted with R³⁰” in the present specification represents an alkenyl group as defined above having a to b pieces of carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with any of R⁴, R¹³, R²³ or R³⁰, and each of the alkenyl groups is selected from within the range of the specified number of carbon atoms. In this case, when the number of substituents R⁴, R¹³, R²³ or R³⁰ on each (C_(a) to C_(b)) alkenyl group is two or more, R⁴s, R¹³s, R²³s or R³⁰s may be the same as or different from each other.

Each expression “(C_(a) to C_(b)) alkynyl optionally substituted with R⁴”, “(C_(a) to C_(b)) alkynyl optionally substituted with R¹³”, “(C_(a) to C_(b)) alkynyl optionally substituted with R²³” or “(C_(a) to C_(b)) alkynyl optionally substituted with R³⁰” in the present specification represents an alkynyl group as defined above having a to b pieces of carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with any of R⁴, R¹³, R²³ or R³⁰, and each of the alkynyl groups is selected from within the range of the specified number of carbon atoms. In this case, when the number of substituents R⁴, R¹³, R²³ or R³⁰ on each (C_(a) to C_(b)) alkynyl group is two or more, R⁴s, R¹³s, R²³s or R³⁰s may be the same as or different from each other.

Specific examples of the expressions in the present specification of (R² together with R¹ may form a C₂ to C₇ alkylene chain to form together with a nitrogen atom to which R¹ and R² are bonded, a 3- to 8-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom and may be optionally substituted with an oxo group or a thioxo group), (R⁷ together with R⁶ may form a C₂ to C₆ alkylene chain to form together with a nitrogen atom to which R⁶ and R⁷ are bonded, a 3- to 7-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom and may be optionally substituted with an oxo group or a thioxo group), (R¹⁷ together with R¹⁶ may form a C_(a) to C_(b) alkylene chain to form together with a nitrogen atom to which R¹⁶ and R¹⁷ are bonded, a d- to e-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom and may be optionally substituted with an oxo group or a thioxo group), (R²⁵ together with R²⁴ may form a C₂ to C₅ alkylene chain to form together with a nitrogen atom to which R²⁴ and R²⁵ are bonded, a 3- to 6-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom and may be optionally substituted with an oxo group or a thioxo group) and the like include an aziridine, an azetidine, an azetidin-2-one, a pyrrolidine, a pyrrolidin-2-one, an oxazolidine, an oxazolidin-2-one, an oxazolidine-2-thione, a thiazolidine, a thiazolidin-2-one, a thiazolidine-2-thione, an imidazolidine, an imidazolidin-2-one, an imidazolidine-2-thione, a piperidine, a piperidin-2-one, a piperidine-2-thione, a 2H-3,4,5,6-tetrahydro-1,3-oxazin-2-one, a 2H-3,4,5,6-tetrahydro-1,3-oxazine-2-thione, a morpholine, a 2H-3,4,5,6-tetrahydro-1,3-thiazin-2-one, a 2H-3,4,5,6-tetrahydro-1,3-thiazine-2-thione, a thiomorpholine, a perhydropyrimidin-2-one, a piperazine, a homopiperidine, a homopiperidin-2-one and a heptamethyleneimine. Each of the rings is selected from within the range of the specified number of carbon atoms.

Specific examples of the expression in the present specification of (R^(2a) together with R^(1a) may form a C₃ to C₆ alkylene chain to form together with a nitrogen atom to which R^(1a) and R^(2a) are bonded, a 4- to 7-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom and may be optionally substituted with an oxo group or a thioxo group) include an azetidin-2-one, a pyrrolidin-2-one, a pyrrolidine-2,5-dione, an oxazolidin-2-one, an oxazolidine-2-thione, an oxazolidine-2,4-dione, a thiazolidin-2-one, a thiazolidine-2-thione, a thiazolidine-2,4-dione, an imidazolidin-2-one, an imidazolidine-2-thione, an imidazolidine-2,4-dione, a piperidin-2-one, a piperidine-2-thione, a piperidine-2,6-dione, a 2H-3,4,5,6-tetrahydro-1,3-oxazin-2-one, a 2H-3,4,5,6-tetrahydro-1,3-oxazine-2-thione, a 2H-3,4,5,6-tetrahydro-1,3-thiazin-2-one, a 2H-3,4,5,6-tetrahydro-1,3-thiazine-2-thione, a perhydropyrimidin-2-one and a homopiperidin-2-one. Each of the rings is selected from within the range of the specified number of carbon atoms.

Specific examples of the expression in the present specification of (R^(2b) together with R^(1b) may form a C₄ to C₅ alkylene chain or a C₄ to C₅ alkenylene chain to form together with a carbon atom to which R^(1b) and R^(2b) are bonded, a 5- to 6-membered ring, and in this case, the alkylene chain or the alkenylene chain may contain one to three oxygen atom(s), sulfur atom(s) or nitrogen atom(s)) include a thiazolidin-2-ylidene, a 2,3-dihydrothiazol-2-ylidene, an imidazolidin-2-ylidene, a 2,3-dihydroimidazol-2-ylidene, a 2,3-dihydro-1,3,4-thiadiazol-2-ylidene, a 1,2-dihydropyridin-2-ylidene, a 2,3-dihydropyridazin-3-ylidene, a 1,2-dihydropyrazin-2-ylidene, a 1,2-dihydropyrimidin-2-ylidene and a 6H-2,3-dihydro-1,3,4-thiadiazin-2-ylidene. Each of the rings is selected from within the range of the specified number of carbon atoms.

Specific examples of the expression in the present specification of (R^(4b) together with R^(4a) may form a C₂ to C₅ alkylene chain to form together with a carbon atom to which R^(4a) and R^(4b) are bonded, a 3- to 6-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom) include a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a tetrahydrofuran ring, a tetrahydrothiophene ring, a pyrrolidine ring, a cyclohexane ring, a tetrahydropyran ring, a tetrahydrothiopyran ring, a piperidine ring, a cycloheptane ring, an oxepane ring, a thiepane ring and an azepane ring. Each of the rings is selected from within the range of the specified number of carbon atoms.

Specific examples of the expressions in the present specification of (R^(7a) together with R^(6a) may form a C₄ to C₆ alkylene chain to form together with a carbon atom to which R^(6a) and R^(7a) are bonded, a 5- to 7-membered ring, and in this case, the alkylene chain may contain one oxygen atom or sulfur atom), (R^(17a) together with R^(16a) may form a C₃ to C₅ alkylene chain to form together with a carbon atom to which R^(16a) and R^(17a) are bonded, a 4- to 6-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom) and the like include a cyclopentylidene, a tetrahydrofuran-3-ylidene, a tetrahydrothiophen-3-ylidene, a cyclohexylidene, a tetrahydropyran-3-ylidene, a tetrahydropyran-4-ylidene, a tetrahydrothiopyran-3-ylidene and a tetrahydrothiopyran-4-ylidene. Each of the rings is selected from within the range of the specified number of carbon atoms.

Specific examples of the expressions in the present specification of (R¹⁰ together with R⁹ may form a C₂ to C₆ alkylene chain to form together with a nitrogen atom to which R⁹ and R¹⁰ are bonded, a 3- to 7-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom), (R^(17b) together with R^(16b) may form a C₃ to C₅ alkylene chain to form together with a nitrogen atom to which R^(16b) and R^(17b) are bonded, a 4- to 6-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom), (R^(17c) together with R^(16c) may form a C₃ to C₅ alkylene chain to form together with a nitrogen atom to which R^(16c) and R^(17c) are bonded, a 4- to 6-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom), (R¹⁹ together with R¹⁸ may form a C₄ to C₇ alkylene chain to form together with a nitrogen atom to which R¹⁸ and R¹⁹ are bonded, a 5- to 8-membered ring, and in this case, the alkylene chain may contain one oxygen atom or sulfur atom), (R²⁹ together with R²⁸ may form a C₂ to C₅ alkylene chain to form together with a nitrogen atom to which R²⁸ and R²⁹ are bonded, a 3- to 6-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom), (R³⁴ together with R³³ may form a C₂ to C₅ alkylene chain to form together with a nitrogen atom to which R³³ and R³⁴ are bonded, a 3- to 6-membered ring, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom) and the like include an aziridine, an azetidine, a pyrrolidine, an oxazolidine, a thiazolidine, an imidazolidine, a piperidine, a morpholine, a thiomorpholine, a piperazine, a homopiperidine and a heptamethyleneimine. Each of the rings is selected from within the range of the specified number of carbon atoms.

In the compounds included in the present invention, examples of the combination of atoms represented by A¹, A², A³ and A⁴ include the following groups:

That is, A-I: A¹, A², A³ and A⁴ are carbon atoms,

A-II: A¹ is a nitrogen atom and A², A³ and A⁴ are carbon atoms,

A-III: A² is a nitrogen atom and A¹, A³ and A⁴ are carbon atoms,

A-IV: A¹ and A³ are nitrogen atoms and A² and A⁴ are carbon atoms,

A-V: A¹ and A² are nitrogen atoms and A³ and A⁴ are carbon atoms,

A-VI: A² and A³ are nitrogen atoms and A¹ and A⁴ are carbon atoms,

A-VII: A² and A⁴ are nitrogen atoms and A¹ and A³ are carbon atoms.

Among them, preferred combinations of atoms represented by A¹, A², A³ and A⁴ are A-I, A-II and A-III, and specifically preferred is A-I.

In the compounds included in the present invention, examples of the substituent represented by G¹ include aromatic 6-membered rings such as a phenyl, a pyridyl, a pyridazinyl, a pyrimidinyl and a pyrazinyl, and aromatic 5-membered rings such as a furyl, a thienyl, an isoxazolyl, an isothiazolyl, a pyrazolyl, an oxazolyl, a thiazolyl and an imidazolyl. Among them, preferred are a phenyl, a pyridyl, a thienyl, a pyrazolyl and a thiazolyl, and specifically preferred is a phenyl. In the compounds included in the present invention, examples of the substituent represented by G² include G²-1 (for example, substituted carbamoyl groups), G²-2 (for example, substituted aminoalkyl groups) and G²-3 to G²-11 (for example, substituted azole groups). Among them, preferred are G²-1, G²-2, G²-4, G²-6, G²-7, G²-9 and G²-10, and specifically preferred are G²-1, G²-2, G²-7 and G²-10.

In the compounds included in the present invention, when G² represents the structure represented by G²-1, examples of the substituent represented by W include an oxygen atom or a sulfur atom.

In the compounds included in the present invention, when G² represents the structure represented by G²-2, examples of the structure represented by L include —C(R^(4a))(R^(4b))—, —C(R^(4a))(R^(4b))CH₂—, —CH₂C(R^(4a))(R^(4b))—, —N(R^(4c))—, —C(R^(4a))(R^(4b))N(R^(4c))— or a single bond. Among them, specifically preferred is —C(R^(4a))(R^(4b))—.

In the compounds included in the present invention, examples of the preferred range of the substituent represented by X include the following groups. In this case, in each of the following cases, when m represents an integer of two or more, Xs may be the same as or different from each other.

That is, X-I: a halogen atom and a trifluoromethyl.

X-II: a halogen atom, a cyano, —SF₅, a C₁ to C₂ haloalkyl, a C₁ to C₂ haloalkoxy and a C₁ to C₂ haloalkylthio.

X-III: a halogen atom, a cyano, a nitro, —SF₅, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₁ to C₄ alkoxy, a C₁ to C₄ haloalkoxy, a C₁ to C₄ alkylthio and a C₁ to C₄ haloalkylthio.

X-IV: a halogen atom, a cyano, a nitro, —SF₅, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a hydroxy(C₁ to C₄) haloalkyl, a C₁ to C₄ alkoxy(C₁ to C₄) haloalkyl, —OR⁵ and —S(O)_(r)R⁵ (where R⁵ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl or a C₁ to C₂ haloalkoxy(C₁ to C₂) haloalkyl, and r represents an integer of 0 to 2).

In the compounds included in the present invention, examples of m representing the number of substituents represented by X include integers of 0 to 5, and among them, m is preferably 1, 2 and 3.

In the compounds included in the present invention, examples of the preferred range of the substituent represented by Y include the following groups. In this case, in each of the following cases, when n represents an integer of two or more, Ys may be the same as or different from each other.

That is, Y-I: a halogen atom, a methyl, an ethyl and a trifluoromethyl.

Y-II: a halogen atom, a nitro and a methyl.

Y-III: a cyano and a nitro.

Y-IV: a halogen atom, a cyano, a nitro, a C₁ to C₂ alkyl, a C₁ to C₂ haloalkyl, a C₁ to C₂ alkoxymethyl, a C₂ to C₃ alkynyl, a C₁ to C₂ haloalkoxy, a C₁ to C₂ haloalkylthio, —N(R⁷)R⁶ (where R⁶ represents a hydrogen atom, a C₁ to C₂ alkyl or a C₁ to C₂ alkylcarbonyl, and R⁷ represents a hydrogen atom or a C₁ to C₂ alkyl) and —C(S)NH₂.

Y-V: a halogen atom, a cyano, a nitro, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₁ to C₂ alkoxy(C₁ to C₂) alkyl, a C₂ to C₄ alkynyl, a C₁ to C₄ alkoxy, a C₁ to C₄ haloalkoxy, a C₁ to C₄ alkylthio, a C₁ to C₄ haloalkylthio, —N(R⁷)R⁶ (where R⁶ represents a hydrogen atom, a C₁ to C₄ alkyl, —CHO, a C₁ to C₄ alkylcarbonyl, a C₁ to C₄ haloalkylcarbonyl, a C₁ to C₄ alkoxycarbonyl, a C₁ to C₄ alkylthiocarbonyl, a C₁ to C₄ alkoxythiocarbonyl or a C₁ to C₄ alkyldithiocarbonyl, and R⁷ represents a hydrogen atom or a C₁ to C₄ alkyl) and —C(S)NH₂.

Y-VI: a halogen atom, a cyano, a nitro, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a (C₁ to C₄) alkyl optionally substituted with R⁴ (where R⁴ represents —OH, a C₁ to C₄ alkoxy, a C₁ to C₄ haloalkoxy, a C₁ to C₄ alkylthio, a C₁ to C₄ haloalkylthio, a C₁ to C₄ alkylsulfinyl, a C₁ to C₄ haloalkylsulfinyl, a C₁ to C₄ alkylsulfonyl or a C₁ to C₄ haloalkylsulfonyl), a C₂ to C₆ alkenyl, a C₂ to C₆ alkynyl, —OR⁵, —S(O)_(r)R⁵ (where R⁵ represents a C₁ to C₄ alkyl or a C₁ to C₄ haloalkyl, and r represents an integer of 0 to 2), —NH₂, —N(R⁷)R⁶ (where R⁶ represents a C₁ to C₄ alkyl, —C(O)R⁸, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹, —C(S)SR⁹ or —S(O)₂R⁹, R⁷ represents a hydrogen atom or a C₁ to C₄ alkyl, R⁸ represents a hydrogen atom, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl or a C₃ to C₆ cycloalkyl, and R⁹ represents a C₁ to C₄ alkyl or a C₁ to C₄ haloalkyl), —C(S)NH₂, D1 to D3, D7, D11 and D22 (where p represents 0).

In the compounds included in the present invention, examples of n representing the number of substituents represented by Y include integers of 0 to 4, and among them, n is preferably 0 and 1.

In the compounds included in the present invention, when G² represents the structure represented by G²-1, examples of the preferred range of the substituent represented by R¹ include the following groups.

That is, R¹-I: a (C₁ to C₂) alkyl substituted with R¹³ (where R¹³ represents a halogen atom, a C₁ to C₃ alkoxy, a C₁ to C₂ haloalkoxy, —C(O)NHR²⁸, D10 or D32, p represents 0, and t represents 0), E4 (where q represents 0) and —N(R¹⁷)R¹⁶ (where R¹⁶ represents a phenyl or D34, R¹⁷ represents a C₁ to C₂ alkyl, and p represents 0).

R¹-II: —CH═NOR¹⁵ (where R¹⁵ represents a C₁ to C₂ alkyl).

R¹-III: —C(O)OR¹⁵ (where R¹⁵ represents a C₁ to C₂ alkyl).

R¹-IV: —C(O)NH₂.

R¹-V: D34 and D35 (where Z represents a halogen atom or a cyano, and p represents an integer of 0 or 1).

R¹-VI: a C₁ to C₄ alkyl, a (C₁ to C₄) alkyl optionally substituted with R¹³ (where R¹³ represents a halogen atom, a cyano, a C₃ to C₄ cycloalkyl, E4, E7, —OR²⁴, —NHR²⁴, —C(R²)═NOR²⁸, —C(O)N(R²⁹)R²⁸, a phenyl, a phenyl substituted with (Z)_(p1), D8, D10, D13, D16, D22, D32 or D34, R¹² represents a methyl, R²¹ represents a methyl, R²⁴ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₁ to C₄ alkylcarbonyl or a C₁ to C₄ alkoxycarbonyl, R²⁷ represents a hydrogen atom or a C₁ to C₂ alkyl, R²⁸ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₃ to C₄ alkenyl or a C₃ to C₄ alkynyl, R²⁹ represents a hydrogen atom or a C₁ to C₂ alkyl, Z represents a halogen atom, a cyano or a nitro, p represents an integer of 0 or 1, p1 represents 1, q represents an integer of 0 or 1, and t represents 0), a C₃ to C₄ cycloalkyl, a cyclopropyl substituted with R¹³ (where R¹³ represents —C(O)N(R²⁹)R²⁸, D10 or D32, R²⁸ represents a C₁ to C₄ haloalkyl, R²⁹ represents a hydrogen atom, p represents 0, and t represents 0), E4, E5 (where q represents 0, and r represents an integer of 0 to 2), a C₃ to C₄ alkenyl, a C₃ to C₄ haloalkenyl and —N(R¹⁷)R¹⁶ (where R¹⁶ represents a phenyl, D32 or D34, R¹⁷ represents a hydrogen atom, a C₁ to C₂ alkyl, a C₃ to C₄ alkenyl or a C₃ to C₄ alkynyl, p represents 0, and t represents 0).

R¹-VII: —CH═NOR¹⁵ (where R¹⁵ represents a C₁ to C₄ alkyl).

R¹-VIII: —C(O)OR¹⁵ and —C(S)OR¹⁵ (where R¹⁵ represents a C₁ to C₄ alkyl).

R¹-IX: —C(O)NHR¹⁶ (where R¹⁶ represents a hydrogen atom, a C₁ to C₄ alkyl or a C₁ to C₄ haloalkyl).

R¹-X: R¹ together with R² forms ═C(R^(2b))R^(1b) (where R^(1b) represents a C₁ to C₄ alkoxy or a C₁ to C₄ alkylthio, R^(2b) represents —NHR^(16c), and R^(16c) represents a hydrogen atom or a C₁ to C₄ alkyl).

R¹-XI: a hydrogen atom, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R¹³ (where R¹³ represents a halogen atom, a cyano, a C₃ to C₄ cycloalkyl, E4, E7, —OR²⁴, —N(R²⁵)R²⁴, —S(O)_(r)R²⁶, a C₁ to C₄ alkylcarbonyl, —C(R²⁷)═NOR²⁸, —C(O)N(R²⁹)R²⁸, —C(S)NH₂, a phenyl, a phenyl substituted with (Z)_(p1), D1, D5, D7, D8, D10, D13, D16, D17, D22, D32 or D34, R¹² represents a C₁ to C₄ alkyl, R²¹ represents a C₁ to C₂ alkyl, R²⁴ represents a hydrogen atom, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, —C(O)R³¹ or —C(O)OR³², R²⁵ represents a hydrogen atom or a C₁ to C₄ haloalkyl, R²⁶ represents a C₁ to C₄ alkyl, R²⁷ represents a hydrogen atom or a C₁ to C₄ alkyl, R²⁸ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a hydroxy(C₁ to C₄) haloalkyl, a C₃ to C₄ cycloalkyl, a C₃ to C₄ alkenyl or a C₃ to C₄ alkynyl, R²⁹ represents a hydrogen atom or a C₁ to C₄ alkyl, R³¹ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl or a C₃ to C₆ cycloalkyl, R³² represents a C₁ to C₄ alkyl or a C₁ to C₄ haloalkyl, Z represents a halogen atom, a cyano, a nitro, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl or a C₁ to C₄ alkoxy, p represents an integer of 0 or 1, p1 represents 1, q represents an integer of 0 or 1, r represents an integer of 0 to 2, and t represents 0), a C₃ to C₆ cycloalkyl, a (C₃ to C₆) cycloalkyl optionally substituted with R¹³ (where R¹³ represents a halogen atom, a cyano, —C(O)N(R²⁹)R²⁸, D10 or D32, R²⁸ represents a C₁ to C₄ haloalkyl, R²⁹ represents a hydrogen atom, p represents 0, and t represents 0), E4, E5, E12 (where q represents 0, and r represents an integer of 0 to 2), a C₃ to C₆ alkenyl, a C₃ to C₆ haloalkenyl and a C₃ to C₆ alkynyl.

R¹-XII: a C₁ to C₆ alkylcarbonyl, —C(OR¹⁵)═NOR¹⁵, —C(NH₂)═NCN, —C(NH₂)═NOR¹⁵ (where R¹⁵ represents a C₁ to C₆ alkyl) and —C(NH₂)═NNO₂.

R¹-XIII: —CH═NOR¹⁵ (where R¹⁵ represents a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl or a C₃ to C₆ alkenyl).

R¹-XIV: —C(O)OR¹⁵ and —C(S)OR¹⁵ (where R¹⁵ represents a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₃ to C₄ cycloalkyl(C₁ to C₄) alkyl or a C₁ to C₄ alkoxycarbonyl(C₁ to C₄) alkyl).

R¹-XV: —C(O)N(R¹⁷)R¹⁶ and —C(S)N(R¹⁷)R¹⁶ (where R¹⁶ represents a hydrogen atom, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R³⁰, a C₃ to C₆ alkenyl, a C₁ to C₆ alkylcarbonyl, a C₁ to C₆ haloalkylcarbonyl or a C₁ to C₆ alkoxycarbonyl, R¹⁷ represents a hydrogen atom or a C₁ to C₆ alkyl, R³⁰ represents a halogen atom, a phenyl substituted with (Z)_(p1) or D32, Z represents a halogen atom, p represents 0, p1 represents 1, and t represents 0).

R¹-XVI: —N(R¹⁷)R¹⁶ (where R¹⁶ represents a C₁ to C₆ haloalkyl, a C₁ to C₆ alkylcarbonyl, a C₁ to C₆ alkoxycarbonyl, a phenyl, a phenyl substituted with (Z)_(p1), D32 or D34, R¹⁷ represents a hydrogen atom, a C₁ to C₆ alkyl, a C₃ to C₆ alkenyl or a C₃ to C₆ alkynyl, Z represents a halogen atom, a cyano or a nitro, p represents 0, p1 represents 1, and t represents 0).

R¹-XVI: a phenyl substituted with (Z)_(P1), D1, D5 to D8, D10, D17 and D32 to D35 (where R¹² represents a C₁ to C₄ alkyl, Z represents a halogen atom, a cyano, a nitro, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl or a C₁ to C₄ alkylsulfonyloxy, p represents an integer of 0 or 1, p1 represents an integer of 1 to 3, and t represents 0).

R¹-XVII: R¹ together with R² forms ═C(R^(2b))R^(1b) (where R^(1b) represents a C₁ to C₆ alkyl, a C₁ to C₆ alkoxy, a C₁ to C₆ haloalkoxy, a C₁ to C₆ alkylthio or —N(R^(17b))R^(16b), R^(2b) represents a C₁ to C₆ alkylthio or —N(R^(17c))R^(16c), or R^(2b) together with R^(1b) may form —N(R^(17c))CH═CHS— to form together with a carbon atom to which R^(1b) and R^(2b) are bonded, a 5-membered ring, R^(16b) represents a cyano, a nitro or a C₁ to C₆ alkoxy, R^(17b) represents a hydrogen atom or a C₁ to C₆ alkyl, R^(16c) represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl or a C₁ to C₆ alkoxy, and R^(17c) represents a hydrogen atom or a C₁ to C₆ alkyl).

In the compounds included in the present invention, when G² represents the structure represented by G²-2, examples of the preferred range of the substituent represented by R^(1a) include the following groups.

That is, R^(1a)-I: —C(O)R¹⁴ (where R¹⁴ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a (C₁ to C₂) alkyl substituted with R³⁰, a C₃ to C₄ cycloalkyl or E4, R³⁰ represents a cyclopropyl, a C₁ to C₂ alkylthio, a C₁ to C₂ alkylsulfinyl or a C₁ to C₂ alkylsulfonyl, p represents 0, and q represents 0).

R^(1a)-II: —C(O)NHR¹⁶ (where R¹⁶ represents a C₁ to C₂ alkyl, a cyclopropyl or a propargyl).

R^(1a)-III: —C(O)R¹⁴ (where R¹⁴ represents a (C₁ to C₄) alkyl optionally substituted with R³⁰, R³⁰ represents —N(R³⁴)R³³ or —C(O)N(R³⁴)R³³, R³³ represents a C₁, to C₄ alkyl or a cyano(C₁ to C₂) alkyl, and R³⁴ represents a hydrogen atom).

R^(1a)-IV: —C(O)R¹⁴ and —C(S)R¹⁴ (where R¹⁴ represents a C₁ to C₄ alkyl, a (C₁ to C₄) alkyl optionally substituted with R³⁰, a C₃ to C₄ cycloalkyl, a C₂ to C₄ alkenyl, a C₂ to C₄ alkynyl or a phenyl substituted with (Z)_(p1), R³⁰ represents a halogen atom or a C₃ to C₄ cycloalkyl, Z represents a halogen atom or a cyano, when p1 represents an integer of two or more, Zs may be the same as or different form each other, and p1 represents an integer of 1 to 3).

R^(1a)-V: —C(O)R¹⁴ and —C(S)R¹⁴ (where R¹⁴ represents a (C₁ to C₄) alkyl optionally substituted with R³⁰, E4 or E5, R³⁰ represents a halogen atom or —S(O)_(r)R³², R³² represents a C₁ to C₄ alkyl or a C₁ to C₄ haloalkyl, q represents 0, and r represents an integer of 0 to 2).

R^(1a)-VI: —C(O)N(R¹⁷)R¹⁶) (where R¹⁶ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₃ to C₄ cycloalkyl or a C₃ to C₄ alkynyl, and R¹⁷ represents a hydrogen atom or a C₁ to C₄ alkyl).

R^(1a)-VII: —C(O)R¹⁴ (where R¹⁴ represents a (C₁ to C₄) alkyl optionally substituted with R³⁰, R³⁰ represents —N(R³⁴)R³³, —N(R³⁴)C(O)R³¹, —N(R³⁴)C(O)OR³² or —C(O)N(R³⁴)R³³, R³¹ represents a C₁ to C₄ haloalkyl, R³² represents a C₁ to C₄ alkyl, R³³ represents a C₁ to C₄ alkyl or a cyano(C₁ to C₂) alkyl, and R³⁴ represents a hydrogen atom or a cyano(C₁ to C₂) alkyl).

R^(1a)-VIII: —C(O)R¹⁴ and —C(S)R¹⁴ (where R¹⁴ represents a C₁ to C₆ alkyl, a C₁ to C₆ alkyl optionally substituted with R³⁰, a C₃ to C₆ cycloalkyl, a C₂ to C₆ alkenyl, a C₂ to C₆ haloalkenyl, a C₂ to C₆ alkynyl, a phenyl substituted with (Z)_(p1) or D32, R³⁰ represents a halogen atom or a C₃ to C₆ cycloalkyl, Z represents a halogen atom, a cyano, a nitro or a C₁ to C₄ alkylthio, when p1 represents an integer of two or more, Zs may be the same as or different form each other, p represents an integer of 0 or 1, p1 represents an integer of 1 to 3, and t represents 0).

R^(1a)-IX: —C(O)R¹⁴ and —C(S)R¹⁴ (where R¹⁴ represents a (C₁ to C₄) alkyl optionally substituted with R³⁰, E4, E5 or E10, R³⁰ represents a halogen atom, a C₁ to C₄ alkoxy, a C₁ to C₄ haloalkoxy, —S(O)_(r)R³², —S(R³²)═NC(O)R³¹ or —S(O)(R³²)═NH, R³¹ represents a C₁ to C₄ haloalkyl, R³² represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl or a cyano(C₁ to C₂) alkyl, q represents 0, and r represents an integer of 0 to 2).

R^(1a)-X: —C(O)OR¹⁵ and —C(O)SR¹⁵ (where R¹⁵ represents a C₁ to C₆ haloalkyl).

R^(1a)-XI: —C(O)N(R¹⁷)R¹⁶ and —C(O)N(R¹⁷)N(R¹⁷)R¹⁶ (where R¹⁶ represents a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₃ to C₆ cycloalkyl or a C₃ to C₆ alkynyl, R¹⁷ represents a hydrogen atom or a C₁ to C₆ alkyl, or R¹⁷ together with R¹⁶ may form a C₃ to C₅ alkylene chain to form together with a nitrogen atom to which R¹⁶ and R¹⁷ are bonded, a 4- to 6-membered ring, and in this case, the alkylene chain may contain one sulfur atom).

In the compounds included in the present invention, when G² represents the structure represented by G²-1, examples of the preferred range of the substituent represented by R² include the following groups.

That is, R²-I: a hydrogen atom.

R²-II: a (C₁ to C₂) alkyl substituted with R^(13a) (where R^(13a) represents —OR²⁴, and R²⁴ represents a C₁ to C₂ alkyl or a C₁ to C₂ alkylcarbonyl).

R²-III: a C₁ to C₃ alkylcarbonyl, a cyclopropylcarbonyl and a C₁ to C₃ alkoxycarbonyl.

R²-IV: a C₁ to C₄ alkyl, a (C₁ to C₂) alkyl substituted with R^(13a) (where R^(13a) represents a cyano, —OR²⁴ or a C₁ to C₄ alkylthio, and R²⁴ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₁ to C₄ alkylcarbonyl or a C₁ to C₄ alkoxycarbonyl), and a C₃ to C₄ alkynyl.

R²-V: —C(O)R^(14a) (where R^(14a) represents a C₁ to C₄ alkyl, a C₁ to C₂ alkoxy(C₁ to C₂) alkyl, a C₃ to C₄ cycloalkyl or a C₂ to C₄ alkenyl).

R²-VI: —C(O)OR^(15a) (where R^(15a) represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl or a C₁ to C₂ alkoxy(C₁ to C₂) alkyl).

R²-VII: a C₁ to C₆ alkyl, a (C₁ to C₄) alkyl substituted with R^(13a) (where R^(13a) represents a cyano, a C₃ to C₄ cycloalkyl, —OR²⁴, —S(O)_(r)R²⁶ or D32, R²⁴ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, —C(O)R³¹ or a C₁ to C₄ alkoxycarbonyl, R²⁶ represents a C₁ to C₄ alkyl, R³¹ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl or a C₃ to C₆ cycloalkyl, p represents 0, r represents an integer of 0 to 2, and t represents 0), a C₃ to C₆ cycloalkyl, a C₃ to C₆ alkenyl and a C₃ to C₆ alkynyl.

R²-VIII: —C(O)R^(14a) (where R^(14a) represents a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₁ to C₄ alkoxy(C₁ to C₄) alkyl, a C₁ to C₄ alkylthio(C₁ to C₄) alkyl, a C₁ to C₄ alkylsulfinyl(C₁ to C₄) alkyl, a C₁ to C₄ alkylsulfonyl(C₁ to C₄) alkyl, a C₃ to C₆ cycloalkyl, a C₂ to C₆ alkenyl, a C₂ to C₆ alkynyl, a phenyl, a phenyl substituted with (Z)_(p1) or D32, Z represents a halogen atom, a cyano, a nitro, a C₁ to C₆ alkyl or C₁ to C₆ alkoxy, p represents 0, p1 represents 1, and t represents 0) and —C(O)C(O)OR^(15a) (where R^(15a) represents a C₁ to C₆ alkyl).

R²-IX: —C(O)OR^(15a) (where R^(15a) represents a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₁ to C₄ alkoxy(C₁ to C₄) alkyl, a C₃ to C₆ alkenyl, a C₃ to C₆ alkynyl or a phenyl).

R²-X: a C₁ to C₆ haloalkylthio.

In the compounds included in the present invention, when G² represents the structure represented by G²-2, examples of the preferred range of the substituent represented by R^(2a) include the following groups.

That is, R^(2a)-I: a hydrogen atom.

R^(2a)-II: a C₁ to C₂ alkyl, a (C₁ to C₂) alkyl substituted with R^(13a) (where R^(13a) represents a cyano, a cyclopropyl or a C₁ to C₂ alkoxy) and a propargyl.

R^(2a)-III: a C₁ to C₄ alkyl, a (C₁ to C₂) alkyl substituted with R^(13a) (where R^(13a) represents a cyano, a C₃ to C₄ cycloalkyl or a C₁ to C₂ alkoxy), a C₃ to C₄ alkenyl and a C₃ to C₄ alkynyl.

R^(2a)-IV: a C₁ to C₆ alkyl, a (C₁ to C₄) alkyl substituted with R^(13a) (where R^(13a) represents a cyano, a C₃ to C₄ cycloalkyl, a C₁ to C₄ alkoxy, a C₁ to C₄ alkylthio or a C₁ to C₄ alkoxycarbonyl), a C₃ to C₆ alkenyl and a C₃ to C₆ alkynyl.

In the compounds included in the present invention, examples of the preferred range of the substituent represented by R³ include the following groups.

That is, R³-I: a trifluoromethyl and a chlorodifluoromethyl.

R³-II: a difluoromethyl, a trifluoromethyl, a chlorodifluoromethyl, a bromodifluoromethyl, a 1,1,2,2-tetrafluoroethyl and a pentafluoroethyl.

R³-III: a C₁ to C₂ haloalkyl.

R³-IV: a C₁ to C₄ haloalkyl optionally substituted with two or more of any halogen atoms.

R³-V: a C₁ to C₄ haloalkyl.

R³-VI: a C₁ to C₆ haloalkyl and a C₃ to C₈ halocycloalkyl.

In the compounds included in the present invention, examples of the preferred range of the substituent represented by R^(3a) include the following groups.

That is, R^(3a)-I: a halogen atom and a methyl.

R^(3a)-II: a halogen atom and a C₁ to C₂ alkyl.

R^(3a)-III: a halogen atom, a C₁ to C₆ alkyl and a C₁ to C₆ alkylthio.

In the compounds included in the present invention, examples of the preferred range of the substituent represented by R^(3b) include the following groups.

That is, R^(3b)-I: a hydrogen atom.

R^(3b)-II: a hydrogen atom and a halogen atom.

In the compounds included in the present invention, examples of the preferred range of the substituent represented by R^(3c) include the following groups.

That is, R^(3c)-I: a hydrogen atom.

R^(3a)-II: a hydrogen atom, a halogen atom and a C₁ to C₂ alkyl.

In the compounds included in the present invention, examples of the preferred range of the substituent represented by R^(4a) include the following groups.

That is, R^(4a)-I: a hydrogen atom, a cyano and a methyl.

R^(4a)-II: a hydrogen atom, a cyano, a methyl and —C(S)NH₂.

R^(4a)-III: a hydrogen atom, a cyano, a C₁ to C₂ alkyl, a C₁ to C₂ haloalkyl, a C₂ to C₄ alkynyl and —C(S)NH₂.

In the compounds included in the present invention, a preferred substituent represented by R^(4b) is a hydrogen atom.

These groups representing the preferred range of each substituent of the compounds included in the present invention may be optionally combined, each of which represents the range of the preferred compound of the present invention.

When G² represents the structure represented by G²-1, examples of the combination of X, Y, R¹ and R² in the preferred range include combinations shown in Table 1. However, the combinations in Table 1 are only for exemplification and the present invention is not limited to these combinations.

In Table, the expression “-” represents unsubstituted.

TABLE 1 X Y R¹ R² X-I — R¹-I R²-I X-I — R¹-I R²-II X-I — R¹-I R²-III X-I — R¹-I R²-VI X-I — R¹-II R²-I X-I — R¹-II R²-II X-I — R¹-II R²-III X-I — R¹-III R²-I X-I — R¹-III R²-III X-I — R¹-IV R²-I X-I — R¹-V R²-I X-I — R¹-V R²-II X-I — R¹-V R²-III X-I — R¹-V R²-IV X-I — R¹-V R²-V X-I — R¹-V R²-VI X-I Y-I R¹-I R²-I X-I Y-I R¹-I R²-II X-I Y-I R¹-I R²-III X-I Y-I R¹-I R²-IV X-I Y-I R¹-I R²-V X-I Y-I R¹-I R²-VI X-I Y-I R¹-I R²-VII X-I Y-I R¹-I R²-VIII X-I Y-I R¹-I R²-IX X-I Y-I R¹-I R²-X X-I Y-I R¹-II R²-I X-I Y-I R¹-II R²-II X-I Y-I R¹-II R²-III X-I Y-I R¹-II R²-IV X-I Y-I R¹-II R²-VI X-I Y-I R¹-II R²-VII X-I Y-I R¹-II R²-IX X-I Y-I R¹-III R²-I X-I Y-I R¹-III R²-III X-I Y-I R¹-III R²-V X-I Y-I R¹-III R²-VI X-I Y-I R¹-III R²-VIII X-I Y-I R¹-III R²-IX X-I Y-I R¹-III R²-X X-I Y-I R¹-IV R²-I X-I Y-I R¹-IV R²-II X-I Y-I R¹-IV R²-III X-I Y-I R¹-IV R²-IV X-I Y-I R¹-IV R²-VI X-I Y-I R¹-IV R²-VII X-I Y-I R¹-IV R²-IX X-I Y-I R¹-V R²-I X-I Y-I R¹-V R²-II X-I Y-I R¹-V R²-III X-I Y-I R¹-V R²-IV X-I Y-I R¹-V R²-V X-I Y-I R¹-V R²-VI X-I Y-I R¹-V R²-VII X-I Y-I R¹-V R²-VIII X-I Y-I R¹-V R²-IX X-I Y-I R¹-V R²-X X-I Y-I R¹-VI R²-I X-I Y-I R¹-VI R²-II X-I Y-I R¹-VI R²-III X-I Y-I R¹-VI R²-IV X-I Y-I R¹-VI R²-V X-I Y-I R¹-VI R²-VI X-I Y-I R¹-VII R²-I X-I Y-I R¹-VII R²-II X-I Y-I R¹-VII R²-III X-I Y-I R¹-VII R²-IV X-I Y-I R¹-VII R²-VI X-I Y-I R¹-VIII R²-I X-I Y-I R¹-VIII R²-III X-I Y-I R¹-VIII R²-V X-I Y-I R¹-VIII R²-VI X-I Y-I R¹-IX R²-I X-I Y-I R¹-IX R²-II X-I Y-I R¹-IX R²-III X-I Y-I R¹-IX R²-IV X-I Y-I R¹-IX R²-VI X-I Y-I R¹-X — X-I Y-I R¹-XI R²-I X-I Y-I R¹-XI R²-II X-I Y-I R¹-XI R²-III X-I Y-I R¹-XII R²-I X-I Y-I R¹-XIII R²-I X-I Y-I R¹-XIII R²-II X-I Y-I R¹-XIII R²-III X-I Y-I R¹-XIV R²-I X-I Y-I R¹-XIV R²-III X-I Y-I R¹-XV R²-I X-I Y-I R¹-XV R²-II X-I Y-I R¹-XV R²-III X-I Y-I R¹-XVI R²-I X-I Y-I R¹-XVI R²-II X-I Y-I R¹-XVI R²-III X-I Y-I R¹-XVII R²-I X-I Y-I R¹-XVII R²-II X-I Y-I R¹-XVII R²-III X-I Y-I R¹-XVIII — X-I Y-IV R¹-I R²-I X-I Y-IV R¹-I R²-II X-I Y-IV R¹-I R²-III X-I Y-IV R¹-I R²-IV X-I Y-IV R¹-I R²-V X-I Y-IV R¹-I R²-VI X-I Y-IV R¹-II R²-I X-I Y-IV R¹-II R²-II X-I Y-IV R¹-II R²-III X-I Y-IV R¹-II R²-IV X-I Y-IV R¹-II R²-VI X-I Y-IV R¹-III R²-I X-I Y-IV R¹-III R²-III X-I Y-IV R¹-III R²-V X-I Y-IV R¹-III R²-VI X-I Y-IV R¹-IV R²-I X-I Y-IV R¹-IV R²-II X-I Y-IV R¹-IV R²-III X-I Y-IV R¹-IV R²-IV X-I Y-IV R¹-IV R²-VI X-I Y-IV R¹-V R²-I X-I Y-IV R¹-V R²-II X-I Y-IV R¹-V R²-III X-I Y-IV R¹-V R²-IV X-I Y-IV R¹-V R²-V X-I Y-IV R¹-V R²-VI X-I Y-IV R¹-VI R²-I X-I Y-IV R¹-VI R²-II X-I Y-IV R¹-VI R²-III X-I Y-IV R¹-VII R²-I X-I Y-IV R¹-VII R²-II X-I Y-IV R¹-VII R²-III X-I Y-IV R¹-VIII R²-I X-I Y-IV R¹-VIII R²-III X-I Y-IV R¹-IX R²-I X-I Y-IV R¹-IX R²-II X-I Y-IV R¹-IX R²-III X-I Y-IV R¹-X — X-I Y-IV R¹-XI R²-I X-I Y-IV R¹-XII R²-I X-I Y-IV R¹-XIII R²-I X-I Y-IV R¹-XIV R²-I X-I Y-IV R¹-XV R²-I X-I Y-IV R¹-XVI R²-I X-I Y-IV R¹-XVII R²-I X-I Y-IV R¹-XVII R²-III X-I Y-IV R¹-XVIII — X-I Y-V R¹-I R²-I X-I Y-V R¹-I R²-II X-I Y-V R¹-I R²-III X-I Y-V R¹-II R²-I X-I Y-V R¹-II R²-II X-I Y-V R¹-II R²-III X-I Y-V R¹-III R²-I X-I Y-V R¹-III R²-III X-I Y-V R¹-IV R²-I X-I Y-V R¹-IV R²-II X-I Y-V R¹-IV R²-III X-I Y-V R¹-V R²-I X-I Y-V R¹-V R²-II X-I Y-V R¹-V R²-III X-I Y-V R¹-VI R²-I X-I Y-V R¹-VII R²-I X-I Y-V R¹-VIII R²-I X-I Y-V R¹-IX R²-I X-I Y-V R¹-X — X-I Y-VI R¹-I R²-I X-I Y-VI R¹-I R²-III X-I Y-VI R¹-II R²-I X-I Y-VI R¹-III R²-I X-I Y-VI R¹-IV R²-I X-I Y-VI R¹-V R²-I X-I Y-VI R¹-V R²-III X-II Y-I R¹-I R²-I X-II Y-I R¹-I R²-II X-II Y-I R¹-I R²-III X-II Y-I R¹-I R²-IV X-II Y-I R¹-I R²-V X-II Y-I R¹-I R²-VI X-II Y-I R¹-II R²-I X-II Y-I R¹-II R²-II X-II Y-I R¹-II R²-III X-II Y-I R¹-II R²-IV X-II Y-I R¹-II R²-VI X-II Y-I R¹-III R²-I X-II Y-I R¹-III R²-III X-II Y-I R¹-III R²-V X-II Y-I R¹-III R²-VI X-II Y-I R¹-IV R²-I X-II Y-I R¹-IV R²-II X-II Y-I R¹-IV R²-III X-II Y-I R¹-IV R²-IV X-II Y-I R¹-IV R²-VI X-II Y-I R¹-V R²-I X-II Y-I R¹-V R²-II X-II Y-I R¹-V R²-III X-II Y-I R¹-V R²-IV X-II Y-I R¹-V R²-V X-II Y-I R¹-V R²-VI X-II Y-I R¹-VI R²-I X-II Y-I R¹-VI R²-II X-II Y-I R¹-VI R²-III X-II Y-I R¹-VII R²-I X-II Y-I R¹-VII R²-II X-II Y-I R¹-VII R²-III X-II Y-I R¹-VIII R²-I X-II Y-I R¹-VIII R²-III X-II Y-I R¹-IX R²-I X-II Y-I R¹-IX R²-II X-II Y-I R¹-IX R²-III X-II Y-I R¹-X — X-II Y-I R¹-XI R²-I X-II Y-I R¹-XII R²-I X-II Y-I R¹-XIII R²-I X-II Y-I R¹-XIV R²-I X-II Y-I R¹-XV R²-I X-II Y-I R¹-XVI R²-I X-II Y-I R¹-XVII R²-I X-II Y-I R¹-XVII R²-III X-II Y-I R¹-XVIII — X-II Y-IV R¹-I R²-I X-II Y-IV R¹-I R²-II X-II Y-IV R¹-I R²-III X-II Y-IV R¹-II R²-I X-II Y-IV R¹-II R²-II X-II Y-IV R¹-II R²-III X-II Y-IV R¹-III R²-I X-II Y-IV R¹-III R²-III X-II Y-IV R¹-IV R²-I X-II Y-IV R¹-IV R²-II X-II Y-IV R¹-IV R²-III X-II Y-IV R¹-V R²-I X-II Y-IV R¹-V R²-II X-II Y-IV R¹-V R²-III X-II Y-IV R¹-VI R²-I X-II Y-IV R¹-VII R²-I X-II Y-IV R¹-VIII R²-I X-II Y-IV R¹-IX R²-I X-II Y-IV R¹-X — X-II Y-V R¹-I R²-I X-II Y-V R¹-I R²-III X-II Y-V R¹-II R²-I X-II Y-V R¹-III R²-I X-II Y-V R¹-IV R²-I X-II Y-V R¹-V R²-I X-II Y-V R¹-V R²-III X-II Y-VI R¹-I R²-I X-II Y-VI R¹-I R²-III X-II Y-VI R¹-II R²-I X-II Y-VI R¹-V R²-III X-III Y-I R¹-I R²-I X-III Y-I R¹-I R²-II X-III Y-I R¹-I R²-III X-III Y-I R¹-II R²-I X-III Y-I R¹-II R²-II X-III Y-I R¹-II R²-III X-III Y-I R¹-III R²-I X-III Y-I R¹-III R²-III X-III Y-I R¹-IV R²-I X-III Y-I R¹-IV R²-II X-III Y-I R¹-IV R²-III X-III Y-I R¹-V R²-I X-III Y-I R¹-V R²-II X-III Y-I R¹-V R²-III X-III Y-I R¹-VI R²-I X-III Y-I R¹-VII R²-I X-III Y-I R¹-VIII R²-I X-III Y-I R¹-IX R²-I X-III Y-I R¹-X — X-III Y-IV R¹-I R²-I X-III Y-IV R¹-I R²-III X-III Y-IV R¹-II R²-I X-III Y-IV R¹-III R²-I X-III Y-IV R¹-IV R²-I X-III Y-IV R¹-V R²-I X-III Y-IV R¹-V R²-III X-III Y-V R¹-I R²-I X-III Y-V R¹-I R²-III X-III Y-V R¹-II R²-I X-III Y-V R¹-V R²-III X-III Y-VI R¹-I R²-I X-III Y-VI R¹-II R²-I X-IV Y-I R¹-I R²-I X-IV Y-I R¹-I R²-III X-IV Y-I R¹-II R²-I X-IV Y-I R¹-III R²-I X-IV Y-I R¹-IV R²-I X-IV Y-I R¹-V R²-I X-IV Y-I R¹-V R²-III X-IV Y-IV R¹-I R²-I X-IV Y-IV R¹-I R²-III X-IV Y-IV R¹-II R²-I X-IV Y-IV R¹-V R²-III X-IV Y-V R¹-I R²-I X-IV Y-V R¹-II R²-I X-IV Y-VI R¹-I R²-I X-IV Y-VI R¹-II R²-I

When G² represents the structure represented by G²-2, examples of the preferred range of the combination of X, Y, R¹ and R² include combinations shown in Table 2. However, the combinations in Table 2 are only for exemplification and the present invention is not limited to these combinations.

In Table, the expression “-” represents unsubstituted.

TABLE 2 X Y R^(1a) R^(2a) X-I — R^(1a)-I R^(2a)-I X-I — R^(1a)-I R^(2a)-II X-I — R^(1a)-I R^(2a)-III X-I — R^(1a)-I R^(2a)-IV X-I — R^(1a)-II R^(2a)-I X-I — R^(1a)-II R^(2a)-II X-I — R^(1a)-III R^(2a)-I X-I — R^(1a)-IV R^(2a)-I X-I — R^(1a)-IV R^(2a)-II X-I — R^(1a)-IV R^(2a)-III X-I — R^(1a)-V R^(2a)-I X-I — R^(1a)-V R^(2a)-II X-I — R^(1a)-V R^(2a)-III X-I — R^(1a)-VI R^(2a)-I X-I — R^(1a)-VII R^(2a)-I X-I — R^(1a)-VIII R^(2a)-I X-I — R^(1a)-VIII R^(2a)-II X-I — R^(1a)-IX R^(2a)-I X-I — R^(1a)-IX R^(2a)-II X-I — R^(1a)-X R^(2a)-I X-I — R^(1a)-XI R^(2a)-I X-I Y-II R^(1a)-I R^(2a)-I X-I Y-II R^(1a)-I R^(2a)-II X-I Y-II R^(1a)-I R^(2a)-III X-I Y-II R^(1a)-I R^(2a)-IV X-I Y-II R^(1a)-II R^(2a)-I X-I Y-II R^(1a)-II R^(2a)-II X-I Y-II R^(1a)-III R^(2a)-I X-I Y-II R^(1a)-IV R^(2a)-I X-I Y-II R^(1a)-IV R^(2a)-II X-I Y-II R^(1a)-IV R^(2a)-III X-I Y-II R^(1a)-V R^(2a)-I X-I Y-II R^(1a)-V R^(2a)-II X-I Y-II R^(1a)-V R^(2a)-III X-I Y-II R^(1a)-VI R^(2a)-I X-I Y-II R^(1a)-VII R^(2a)-I X-I Y-II R^(1a)-VIII R^(2a)-I X-I Y-II R^(1a)-VIII R^(2a)-II X-I Y-II R^(1a)-IX R^(2a)-I X-I Y-II R^(1a)-IX R^(2a)-II X-I Y-II R^(1a)-X R^(2a)-I X-I Y-II R^(1a)-XI R^(2a)-I X-I Y-IV R^(1a)-I R^(2a)-I X-I Y-IV R^(1a)-I R^(2a)-II X-I Y-IV R^(1a)-I R^(2a)-III X-I Y-IV R^(1a)-II R^(2a)-I X-I Y-IV R^(1a)-III R^(2a)-I X-I Y-IV R^(1a)-IV R^(2a)-I X-I Y-IV R^(1a)-IV R^(2a)-II X-I Y-IV R^(1a)-V R^(2a)-I X-I Y-IV R^(1a)-V R^(2a)-II X-I Y-IV R^(1a)-VI R^(2a)-I X-I Y-IV R^(1a)-VII R^(2a)-I X-I Y-IV R^(1a)-VIII R^(2a)-I X-I Y-IV R^(1a)-IX R^(2a)-I X-I Y-IV R^(1a)-X R^(2a)-I X-I Y-IV R^(1a)-XI R^(2a)-I X-I Y-V R^(1a)-I R^(2a)-I X-I Y-V R^(1a)-I R^(2a)-II X-I Y-V R^(1a)-II R^(2a)-I X-I Y-V R^(1a)-III R^(2a)-I X-I Y-V R^(1a)-IV R^(2a)-I X-I Y-V R^(1a)-V R^(2a)-I X-I Y-V R^(1a)-VI R^(2a)-I X-I Y-VI R^(1a)-I R^(2a)-I X-I Y-VI R^(1a)-II R^(2a)-I X-II Y-II R^(1a)-I R^(2a)-I X-II Y-II R^(1a)-I R^(2a)-II X-II Y-II R^(1a)-I R^(2a)-III X-II Y-II R^(1a)-II R^(2a)-I X-II Y-II R^(1a)-III R^(2a)-I X-II Y-II R^(1a)-IV R^(2a)-I X-II Y-II R^(1a)-IV R^(2a)-II X-II Y-II R^(1a)-V R^(2a)-I X-II Y-II R^(1a)-V R^(2a)-II X-II Y-II R^(1a)-VI R^(2a)-I X-II Y-II R^(1a)-VII R^(2a)-I X-II Y-II R^(1a)-VIII R^(2a)-I X-II Y-II R^(1a)-IX R^(2a)-I X-II Y-II R^(1a)-X R^(2a)-I X-II Y-II R^(1a)-XI R^(2a)-I X-II Y-IV R^(1a)-I R^(2a)-I X-II Y-IV R^(1a)-I R^(2a)-II X-II Y-IV R^(1a)-II R^(2a)-I X-II Y-IV R^(1a)-III R^(2a)-I X-II Y-IV R^(1a)-IV R^(2a)-I X-II Y-IV R^(1a)-V R^(2a)-I X-II Y-IV R^(1a)-VI R^(2a)-I X-II Y-IV R^(1a)-VII R^(2a)-I X-II Y-IV R^(1a)-VIII R^(2a)-I X-II Y-IV R^(1a)-IX R^(2a)-I X-II Y-IV R^(1a)-X R^(2a)-I X-II Y-IV R^(1a)-XI R^(2a)-I X-II Y-V R^(1a)-I R^(2a)-I X-II Y-V R^(1a)-II R^(2a)-I X-II Y-VI R^(1a)-I R^(2a)-I X-II Y-VI R^(1a)-II R^(2a)-I X-III Y-II R^(1a)-I R^(2a)-I X-III Y-II R^(1a)-I R^(2a)-II X-III Y-II R^(1a)-II R^(2a)-I X-III Y-II R^(1a)-III R^(2a)-I X-III Y-II R^(1a)-IV R^(2a)-I X-III Y-II R^(1a)-V R^(2a)-I X-III Y-II R^(1a)-VI R^(2a)-I X-III Y-IV R^(1a)-I R^(2a)-I X-III Y-IV R^(1a)-II R^(2a)-I X-III Y-V R^(1a)-I R^(2a)-I X-III Y-V R^(1a)-II R^(2a)-I X-III Y-VI R^(1a)-I R^(2a)-I X-III Y-VI R^(1a)-II R^(2a)-I X-IV Y-II R^(1a)-I R^(2a)-I X-IV Y-II R^(1a)-II R^(2a)-I X-IV Y-IV R^(1a)-I R^(2a)-I X-IV Y-IV R^(1a)-II R^(2a)-I X-IV Y-V R^(1a)-I R^(2a)-I X-IV Y-V R^(1a)-II R^(2a)-I X-IV Y-VI R^(1a)-I R^(2a)-I X-IV Y-VI R^(1a)-II R^(2a)-I

The compounds of the present invention can be produced, for example, by the following methods.

By reacting 1 equivalent of a compound represented by General Formula (6) (where A¹, A², A³, A⁴, G¹, X, Y, R³, R^(3a), R^(3b), m, n represent the same as the respective definitions in the above and J¹ represents a chlorine atom, a bromine atom, a C₁ to C₄ alkylcarbonyloxy group (for example, a pivaloyloxy group), a C₁ to C₄ alkoxycarbonyloxy group (for example, an isobutyloxycarbonyloxy group) or an azolyl group (for example, an imidazol-1-yl group)) which can be synthesized from a compound represented by General Formula (5) (where A¹, A², A³, A⁴, G¹, X, Y, R³, R^(3a), R^(3b), m and n represent the same as the respective definitions in the above) by using methods known in the literature, for example, a method of reacting with a halogenating agent such as thionyl chloride, phosphorus pentachloride or oxalyl chloride according to the method described in Journal of Medicinal Chemistry (J. Med. Chem.), vol. 34, p. 1630 (1991) and the like, a method of reacting with a halogenated organic acid such as pivaloyl chloride or isobutyl chloroformate, if necessary in the presence of a base, according to the methods described in Tetrahedron Letters (Tetrahedron Lett.), vol. 44, p. 4819 (2003), Journal of Medicinal Chemistry (J. Med. Chem.), vol. 34, p. 222 (1991) and the like, or a method of reacting with carbonyldiimidazole, sulfonyldiimidazole or the like according to The Journal of Organic Chemistry (J. Org. Chem.), vol. 54, p. 5620 (1989), and 1 to 10 equivalent(s) of a compound represented by General Formula (7) (where R¹ and R² represent the same as the respective definitions in the above), if necessary using a solvent such as dichloromethane, chloroform, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethyl acetate or acetonitrile, if necessary in the presence of 1 to 2 equivalent(s) of a base such as potassium carbonate, triethylamine, pyridine or 4-(dimethylamino)pyridine with respect to 1 equivalent of the compound represented by General Formula (6), at a temperature ranging from 0° C. to a reflux temperature of the solvent for 10 minutes to 24 hours, a compound of the present invention represented by General Formula (1-1) (where A¹, A², A³, A⁴, G¹, Y, R¹, R², R³, R^(3a), R^(3b), m and n represent the same as the respective definitions in the above) corresponding to General Formula (1) in which G² is G²-1 and W is an oxygen atom can be synthesized.

Furthermore, by reacting 1 equivalent of the compound represented by General Formula (5) and 1 to 20 equivalent(s) of the compound represented by General Formula (7), if necessary using a solvent such as dichloromethane, chloroform, diethyl ether, tetrahydrofuran or 1,4-dioxane, if necessary in the presence of 1 to 4 equivalent(s) of a base such as potassium carbonate, triethylamine, pyridine or 4-(dimethylamino)pyridine with respect to 1 equivalent of the compound represented by General Formula (5), using 1 to 4 equivalent(s) of a condensing agent such as WSC (1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride) or CDI (carbonyldiimidazole) with respect to 1 equivalent of the compound represented by General Formula (5) at a temperature ranging from 0° C. to a reflux temperature of the solvent for 10 minutes to 24 hours, the compound of the present invention represented by General Formula (1-1) can be also obtained.

By reacting 1 equivalent of a compound of the present invention represented by General Formula (1-2) (where A¹, A², A³, A⁴, G¹, X, Y, R³, R^(3a), R^(3b), m and n represent the same as the respective definitions in the above) corresponding to General Formula (1) in which G² is G²-1, W is an oxygen atom, and R¹ and R² are hydrogen atoms, and 2 to 10 equivalents of a compound represented by General Formula (8) (where R¹⁴, R^(16c) and R^(17c) represent the same as the respective definitions in the above and R represents a C₁ to C₆ alkyl), if necessary under an atmosphere of an inert gas such as nitrogen or argon, without solvent or with a solvent such as benzene or toluene at a temperature ranging from room temperature to a reflux temperature of the solvent for 1 hour to 24 hours, a compound of the present invention represented by General Formula (1-3) (where A¹, A², A³, A⁴, G¹, X, Y, R³, R^(3a), R^(3b), R¹⁴, R^(16c), R^(17c), m and n represent the same as the respective definitions in the above) corresponding to General Formula (1) in which G² is G²-1, W is an oxygen atom, and R² together with R¹ forms ═C(R¹⁴)N(R^(17c))R^(16c) can be obtained.

The compounds represented by General Formula (8) used here are known compounds and some of them are commercially available. The others can be easily synthesized by methods known in the literature, for example, The Journal of Organic Chemistry (J. Org. Chem.), vol. 49, p. 3659 (1984).

By reacting 1 equivalent of the compound of the present invention represented by General Formula (1-3) obtained in such a manner and 1 to 5 equivalent(s) of alkoxyamines represented by General Formula (9) (where R¹⁵ represents the same as the definition in the above) or salts thereof, if necessary using a solvent such as methanol, ethanol, diethyl ether, tetrahydrofuran or 1,4-dioxane, furthermore, when the compound represented by General Formula (9) is a salt, if necessary with the addition of 1 to 4 equivalent(s) of a base such as triethylamine or 1,8-diazabicyclo(5,4,0)-7-undecene, at a temperature ranging from room temperature to a reflux temperature of the solvent for 10 minutes to 24 hours, a compound of the present invention represented by General Formula (1-4) (where A¹, A², A³, A⁴, G¹, X, Y, R³, R^(3a), R^(3b), R¹⁴, R¹⁵, m and n represent the same as the respective definitions in the above) corresponding to General Formula (1) in which G² is G²-1, W is an oxygen atom, R¹ is —C(R¹⁴)═NOR¹⁵, and R² is a hydrogen atom can be obtained.

The compounds represented by General Formula (9) used here are known compounds and some of them are commercially available. The others can be easily synthesized according to methods known in the literature, for example, The Journal of Organic Chemistry (J. Org. Chem.), vol. 70, p. 6991 (2005).

To a compound of the present invention represented by General Formula (1-2) (where A¹, A², A³, A⁴, G¹, X, Y, R³, R^(3a), R^(3b), m and n represent the same as the respective definitions in the above) corresponding to General Formula (1) in which G² is G²-1, W is an oxygen atom, and R¹ and R² are hydrogen atoms, under an atmosphere of an inert gas such as nitrogen or argon, if necessary using a solvent such as toluene, dichloromethane or 1,2-dichloroethane, 1 to 1.5 equivalent(s) of oxalyl chloride with respect to 1 equivalent of the compound of the present invention represented by General Formula (1-2) is added at a temperature ranging from 0° C. to room temperature. Subsequently, by reacting the mixture at a temperature ranging from room temperature to a reflux temperature of the solvent for 1 hour to 24 hours, a substituted acyl isocyanate represented by General Formula (10) (where A¹, A², A³, A⁴, G¹, X, Y, R³, R^(3a), R^(3b), m and n represent the same as the respective definitions in the above) can be obtained.

By reacting 1 equivalent of the substituted acyl isocyanate represented by General Formula (10) obtained in such a manner and 1 to 20 equivalent(s) of an alcohol or a thiol represented by General Formula (11) (where W^(a) represents an oxygen atom or a sulfur atom, and R¹⁵ represents the same as the definition in the above), if necessary in the presence of 1 to 4 equivalent(s) of a base such as potassium carbonate, triethylamine, pyridine or 4-(dimethylamino)pyridine, if necessary using a solvent such as benzene, toluene, dichloromethane, chloroform, diethyl ether, tetrahydrofuran or 1,4-dioxane, at a temperature ranging from 0° C. to a reflux temperature of the solvent for 10 minutes to 24 hours, a compound of the present invention represented by General Formula (1-5) (where A¹, A², A³, A⁴, G¹, X, Y, R³, R^(3a), R^(3b), R¹⁵, m and n represent the same as the respective definitions in the above, and W^(a) represents an oxygen atom or a sulfur atom) corresponding to General Formula (1) in which G² is G²-1, W is an oxygen atom, R¹ is —C(O)—W^(a)—R¹⁵, and R² is a hydrogen atom can be obtained.

The compounds represented by General Formula (11) used here are known compounds and some of them are commercially available. The others can be easily synthesized according to general synthetic methods for alcohols and thiols described in the literature.

By reacting 1 equivalent of the substituted acyl isocyanate represented by General Formula (10) (where A¹, A², A³, A⁴, G¹, X, Y, R³, R^(3a), R^(3b), m and n represent the same as the respective definitions in the above) used in Production Method C and 1 to 20 equivalent(s) of a primary or secondary amine represented by General Formula (12) (where R¹⁶ and R¹⁷ represent the same as the respective definitions in the above), if necessary using a solvent such as benzene, toluene, dichloromethane, chloroform, diethyl ether, tetrahydrofuran or 1,4-dioxane, at a temperature ranging from 0° C. to a reflux temperature of the solvent for 10 minutes to 24 hours, a compound of the present invention represented by General Formula (1-6) (where A¹, A², A³, A⁴, G¹, X, Y, R³, R^(3a), R^(3b), R¹⁶, R¹⁷, m and n represent the same as the respective definitions in the above) corresponding to General Formula (1) in which G² is G²-1, W is an oxygen atom, R¹ is —C(O)N(R¹⁷)R¹⁶, and R² is a hydrogen atom can be obtained.

To the compound represented by General Formula (6) (where A¹, A², A³, A⁴, G¹, X, Y, R³, R^(3a), R^(3b), m, n and J¹ represent the same as the respective definitions in the above) used in Production Method A, for example, under an atmosphere of an inert gas such as nitrogen or argon, if necessary using a solvent such as benzene, toluene, dichloromethane, acetone or acetonitrile, 1 to 1.5 equivalent(s) of potassium thiocyanate, sodium thiocyanate or ammonium thiocyanate with respect to 1 equivalent of the compound represented by General Formula (6) is added at a temperature ranging from 0° C. to room temperature. Subsequently, by reacting the mixture at a temperature ranging from room temperature to a reflux temperature of the solvent for 10 minutes to 24 hours, a substituted acyl isothiocyanate represented by General Formula (13) (where A¹, A², A³, A⁴, G¹, X, Y, R³, R^(3a), R^(3b), m and n represent the same as the respective definitions in the above) can be obtained.

By reacting the substituted acyl isothiocyanate represented by General Formula (13) obtained in such a manner and an alcohol or a thiol represented by General Formula (11) (where W^(a) and R¹⁵ represent the same as the respective definitions in the above) under substantially the same condition as that in Production Method C, a compound of the present invention represented by General Formula (1-7) (where A¹, A², A³, A⁴, G¹, W^(a), Y, R³, R^(3a), R^(3b), R¹⁵, m and n represent the same as the respective definitions in the above) corresponding to General Formula (1) in which G² is G²-1, W is an oxygen atom, R¹ is —C(S)—W^(a)—R¹⁵, and R² is a hydrogen atom can be obtained.

By reacting the substituted acyl isothiocyanate represented by General Formula (13) (where A¹, A², A³, A⁴, G¹, X, Y, R³, R^(3a), R^(3b), m and n represent the same as the respective definitions in the above) used in Production Method E and a primary or secondary amine represented by General Formula (12) (where R¹⁶ and R¹⁷ represent the same as the respective definitions in the above) under substantially the same condition as that in Production Method D, a compound of the present invention represented by General Formula (1-8) (where A¹, A², A³, A⁴, G¹, X, Y, R³, R^(3a), R^(3b), R¹⁶, R¹⁷, m and n represent the same as the respective definitions in the above) corresponding to General Formula (1) in which G² is G²-1, W is an oxygen atom, R¹ is —C(S)N(R¹⁷)R¹⁶, and R² is a hydrogen atom can be obtained.

By reacting 1 equivalent of a compound of the present invention represented by General Formula (1-9) (where A¹, A², A³, A⁴, G¹, X, Y, R¹, R³, R^(3a), R^(3b), m and n represent the same as the respective definitions in the above) corresponding to General Formula (1) in which G² is G²-1, W is an oxygen atom, and R² is a hydrogen atom and 1 to 10 equivalent(s) of a compound represented by General Formula (14) (where R² is the same definition in the above except a hydrogen atom, J² represents a favorable leaving group such as a chlorine atom, a bromine atom, an iodine atom, a C₁ to C₄ alkylcarbonyloxy group (for example, a pivaloyloxy group), a C₁ to C₄ alkyl sulfonate group (for example, a methanesulfonyloxy group), a C₁ to C₄ haloalkyl sulfonate group (for example, a trifluoromethanesulfonyloxy group), an aryl sulfonate group (for example, a benzenesulfonyloxy group and a p-toluenesulfonyloxy group) or an azolyl group (for example, an imidazol-1-yl group)), if necessary in the presence of 1 to 3 equivalent(s) of a base such as sodium hydride, potassium tertiary butoxide, potassium hydroxide, potassium carbonate, triethylamine or pyridine with respect to 1 equivalent of the compound of the present invention represented by General Formula (1-9), if necessary using a polar solvent such as tetrahydrofuran, 1,4-dioxane, acetonitrile or N,N-dimethylformamide, at a temperature ranging from 0 to 90° C. for 10 minutes to 24 hours, a compound of the present invention represented by General Formula (1-1) (where A¹, A², A³, A⁴, G¹, X, Y, R¹, R³, R^(3a), R^(3b), m and n represent the same as the respective definitions in the above, and R² is the same definition in the above except a hydrogen atom) corresponding to General Formula (1) in which G² is G²-1, and W is an oxygen atom can be obtained.

By reacting the compound of the present invention represented by General Formula (1-7) (where A¹, A², A³, A⁴, G¹, W^(a), X, Y, R³, R^(3a), R^(3b), R¹⁵, m and n represent the same as the respective definitions in the above) corresponding to General Formula (1) in which G² is G²-1, W is an oxygen atom, R¹ is —C(S)—W^(a)—R¹⁵, and R² is a hydrogen atom and a compound represented by General Formula (15) (where R^(15a) represents the same as the definition in the above, and J³ represents a chlorine atom, a bromine atom, an iodine atom or the like) under substantially the same condition as that in Production Method G, a compound of the present invention represented by General Formula (1-10) (where A¹, A², A³, A⁴, G¹, W^(a), X, Y, R³, R^(3a), R^(3b), R¹⁵, R^(15a), m and n represent the same as the respective definitions in the above) corresponding to General Formula (1) in which G² is G²-1, W is an oxygen atom, R² together with R¹ forms ═C(SR^(15a))—W^(a)—R¹⁵ can be obtained.

By reacting 1 equivalent of the compound of the present invention represented by General Formula (1-10) obtained in such a manner and 1 to 50 equivalent(s) of a primary or secondary amine represented by General Formula (16) (where R^(16c) and R^(17c) represent the same as the respective definitions in the above) or a salt thereof, if necessary in the presence of 1 to 20 equivalent(s) of a base such as potassium carbonate, sodium hydrogen carbonate, triethylamine, diisopropylethylamine or pyridine with respect to 1 equivalent of the compound of the present invention represented by General Formula (1-10), if necessary using toluene, dichloromethane, chloroform, methanol, ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethyl acetate, N,N-dimethylformamide, acetic acid, acetonitrile, water or the like or a mixture thereof at any ratio as solvent, at a temperature ranging from 0° C. to a reflux temperature of the solvent for 5 minutes to 24 hours, a compound of the present invention represented by General Formula (1-11) (where A¹, A², A³, A⁴, G¹, W^(a), X, Y, R³, R^(3a), R^(3b), R¹⁵, R^(16c), R^(17c), m and n represent the same as the respective definitions in the above) corresponding to General Formula (1) in which G² is G²-1, W is an oxygen atom, R² together with R¹ forms ═C(N(R^(17c))R^(16c))—W^(a)—R¹⁵ can be obtained.

By reacting 1 equivalent of a compound of the present invention represented by General Formula (1-1) (where A¹, A², A³, A⁴, G¹, X, Y, R¹, R², R³, R^(3a), R^(3b), m and n represent the same as the respective definitions in the above) corresponding to General Formula (1) in which G² is G²-1 and W is an oxygen atom and 1 to 10 equivalent(s) of a sulfurizing agent such as diphosphorus pentasulfide, diphosphorus pentasulfide-HMDO (hexamethyldisiloxane) or Lawesson's Reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide), if necessary in the presence of 1 to 4 equivalent(s) of a base such as sodium hydrogen carbonate, triethylamine or pyridine with respect to 1 equivalent of the compound of the present invention represented by General Formula (1-1), if necessary using a solvent such as benzene, toluene, chlorobenzene, dichloromethane, chloroform, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane or HMPA, at a temperature ranging from room temperature to a reflux temperature of the reaction mixture for 10 minutes to 50 hours, or in pyridine as solvent at a temperature ranging from 80° C. to a reflux temperature the reaction mixture for 1 to 3 hours, a compound of the present invention represented by General Formula (1-12) (where A¹, A², A³, A⁴, G¹, X, Y, R¹, R², R³, R^(3a), R^(3b), m and n represent the same as the respective definitions in the above) corresponding to General Formula (1) in which G² is G²-1 and W is a sulfur atom can be obtained.

By reacting a compound represented by General Formula (17) (where A¹, A², A³, A⁴, G¹, G², X, Y, R³, m and n represent the same as the respective definitions in the above), if necessary using a solvent such as diethyl ether, tetrahydrofuran or tetrahydrofuran-hexane, with 1 to 3 equivalent(s) of a strong base such as lithium aluminium hydride, lithium diisopropylamide or lithium hexamethyldisilazane with respect to 1 equivalent of the compound represented by General Formula (17) at a temperature ranging from −20° C. to room temperature for 1 minute to 1 hour, a compound of the present invention represented by General Formula (2-1) (where A¹, A², A³, A⁴, G¹, G², X, Y, R³, m and n represent the same as the respective definitions in the above) corresponding to General Formula (2) in which R^(3c) is a hydrogen atom can be obtained.

By reacting the compound of the present invention represented by General Formula (2-1) obtained in such a manner, if necessary using a solvent such as benzene, toluene, t-butyl methyl ether or tetrahydrofuran, with 1 to 2 equivalent(s) of a halogenating agent such as N-chlorosuccinimide, N-bromosuccinimide or bromine with respect to 1 equivalent of the compound of the present invention represented by General Formula (2-1) at a temperature ranging from 0 to 50° C. for 15 minutes to 24 hours, a compound of the present invention represented by General Formula (1-13) (where A¹, A², A³, A⁴, G¹, G², X, Y, R³, m and n represent the same as the respective definitions in the above and R^(3a) represents a chlorine atom, bromine atom or iodine atom) corresponding to General Formula (1) in which R^(3b) is a hydrogen atom can be obtained.

To a compound represented by General Formula (17) (where A¹, A², A³, A⁴, G¹, G², X, Y, R³, m and n represent the same as the respective definitions in the above) in a solvent such as tetrahydrofuran or tetrahydrofuran-hexane, 1 to 2 equivalent(s) of a base such as lithium diisopropylamide or lithium hexamethyldisilazane with respect to 1 equivalent of the compound represented by General Formula (17) is added at a temperature ranging from −78° C. to −20° C. Subsequently, by reacting the mixture with 1 to 10 equivalent(s) of a compound represented by General Formula (18) (where R^(3a) represents a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₆ haloalkyl group, a C₃ to C₆ alkenyl group, a C₃ to C₆ alkynyl group or the like, and J⁴ represents a chlorine atom, a bromine atom, an iodine atom, a C₁ to C₄ alkyl sulfonate group (for example, a methanesulfonyloxy group), a C₁ to C₄ haloalkyl sulfonate group (for example, a trifluoromethanesulfonyloxy group), a succinimide group or the like) with respect to 1 equivalent of the compound represented by General Formula (17) at a temperature ranging from −78° C. to −20° C. for 15 minutes to 5 hours, a compound of the present invention represented by General Formula (1-13) (where A¹, A², A³, A⁴, G¹, G², X, Y, R³, m and n represent the same as the respective definitions in the above, and R^(3a) represents a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₆ haloalkyl group, a C₃ to C₆ alkenyl group, a C₃ to C₆ alkynyl group or the like) corresponding to General Formula (1) in which R^(3b) is a hydrogen atom can be obtained.

By reacting a compound of the present invention represented by General Formula (1-14) (where A¹, A², A³, A⁴, G¹, L, X, Y, R^(1a), R³, R^(3a), m and n represent the same as the respective definitions in the above) corresponding to General Formula (1) in which G² is G²-2, R^(3b) is a hydrogen atom, and R^(2a) is a tert-butoxycarbonyl group under a common condition of elimination reaction of a tert-butoxycarbonyl group according to methods known in the literature, for example, Synthesis, p. 480 (1994) and Tetrahedron Letters (Tetrahedron Lett.), vol. 39, p. 4869 (1998), a compound of the present invention represented by General Formula (1-15) (where A¹, A², A³, A⁴, G¹, L, X, Y, R^(1a), R³, R^(3a), m and n represent the same as the respective definitions in the above) corresponding to General Formula (1) in which G² is G²-2, and R^(2a) and R^(3b) are hydrogen atoms can be synthesized.

By reacting a compound of the present invention represented by General Formula (1-16) (where A¹, A², A³, A⁴, G¹, L, X, Y, R^(2a), R³, R^(3a), R^(3b), R¹⁴, m and n represent the same as the respective definitions in the above) corresponding to General Formula (1) in which G² is G²-2 and R^(1a) is —C(O)R¹⁴, and a sulfurizing agent such as diphosphorus pentasulfide, diphosphorus pentasulfide-hexamethyldisiloxane (HMDO) or Lawesson's Reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide) under substantially the same condition as that in Production Method I, a compound of the present invention represented by General Formula (1-17) (where A¹, A², A³, A⁴, G¹, L, X, Y, R^(2a), R³, R^(3a), R^(3b), R¹⁴, m and n represent the same as the respective definitions in the above) corresponding to General Formula (1) in which G² is G²-2 and R^(1a) is —C(S)R¹⁴ can be obtained.

In Production Method A to Production Method M, the objective compounds of the present invention can be obtained by subjecting the reaction mixture after the completion of the reaction to a common after treatment: for example, the reaction mixture is directly concentrated; or dissolved in an organic solvent, washed with water, and then concentrated; or poured into ice water, extracted with an organic solvent, and then concentrated. Furthermore, when purification is required, the objective compound can be separated and purified by any purification method such as recrystallization, column chromatography, thin layer chromatography or preparative liquid chromatography.

The compound represented by General Formula (5) used in Production Method A can be synthesized, for example, according to Reaction Formula 1 and Reaction Formula 2 below.

By hydrolyzing a compound represented by General Formula (21) (where A¹, A², A³, A⁴, G¹, X, Y, R³, m, n and R represent the same as the respective definitions in the above, and R^(3a) represents a chlorine atom, a bromine atom or an iodine atom), which is obtained by reacting a known compound represented by General Formula (19) (where A¹, A², A³, A⁴, G¹, X, Y, R³, m and n represent the same as the respective definitions in the above, and R represents a C₁ to C₆ alkyl group) described in International Patent Application Publication (WO 2005/085216), Japanese Patent Application Publication (JP 2007/308471) and the like under substantially the same condition as that in Production Method J, according to a common condition for ester hydrolysis known in the literature, for example, the reaction condition described in Angewandte Chemie (Angew. Chem.), vol. 63, p. 329 (1951) or Journal of the American Chemical Society (J. Am. Chem. Soc.), vol. 51, p. 1865 (1929), a compound represented by General Formula (5-1) (where A¹, A², A³, A⁴, G¹, X, Y, R³, m and n represent the same as the respective definitions in the above, and R^(3a) represents a chlorine atom, a bromine atom or an iodine atom) corresponding to General Formula (5) in which R^(3b) is a hydrogen atom can be obtained.

By hydrolyzing a compound represented by General Formula (21) (where A¹, A², A³, A⁴, G¹, X, Y, R³, m, n and R represent the same as the respective definitions in the above, and R^(3a) represents a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₆ haloalkyl group, a C₃ to C₆ alkenyl group, a C₃ to C₆ alkynyl group or the like), which is obtained by reacting a known compound represented by General Formula (19) (where A¹, A², A³, A⁴, G¹, X, Y, R³, m and n represent the same as the respective definitions in the above, and R represents a C₁ to C₆ alkyl group) described in International Patent Application Publication (WO 2005/085216), Japanese Patent Application Publication (JP 2007/308471) and the like under substantially the same condition as that in Production Method K, according to a common condition for an ester hydrolysis reaction known in the literature similar to Reaction Formula 1, a compound represented by General Formula (5-1) (where A¹, A², A³, A⁴, G¹, X, Y, R³, m and n represent the same as the respective definitions in the above, and R^(3a) represents a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₆ haloalkyl group, a C₃ to C₆ alkenyl group, a C₃ to C₆ alkynyl group or the like) corresponding to General Formula (5) in which R^(3b) is a hydrogen atom can be obtained.

Some of the compounds represented by General Formula (7) used in Production Method A, the compounds represented by General Formula (12) used in Production Method D and Production Method F and the compounds represented by General Formula (16) used in Production Method H are known compounds and some of them are commercially available. The others can be easily synthesized according to known methods described in the literature, for example, Canadian Journal of Chemistry (Can. J. Chem.), vol. 57, p. 1253 (1979), Journal of the Chemical Society, Chemical Communications (J. Chem. Soc., Chem. Commun.), p. 114 (1987), The Journal of Organic Chemistry (J. Org. Chem.), vol. 50, p. 3243 (1985) and vol. 60, p. 8124 (1995), Synlett, p. 2214, (2005), International Patent Application Publication (WO 2002/062805) and Japanese Patent Application Publication (JP 10/130,221).

Some of the compounds represented by General Formula (14) used in Production Method G, the compounds represented by General Formula (15) used in Production Method H and the compounds represented by General Formula (18) used in Production Method K are known compounds and some of them are commercially available. The others can be easily synthesized according to general synthetic methods described in the literature, for example, methods described in Chemical and Pharmaceutical Bulletin (Chem. Pharm. Bull.), vol. 34, p. 540 (1986) and vol. 49, p. 1102 (2001), Journal of the American Chemical Society (J. Am. Chem. Soc.), vol. 86, p. 4383 (1964), The Journal of Organic Chemistry (J. Org. Chem.), vol. 48, p. 5280 (1983), Organic Synthesis (Org. Synth.), Collective vol. 6, p. 101 (1988), Synlett, p. 2847, (2005), Synthesis, p. 1159, (1990), Japanese Patent Application Publication (JP 05/125017), European Patent Publication (EP 0,051,273) and UK Patent Publication (GB 2,161,802).

The compounds represented by General Formula (17) used in Production Method J and Production Method K are known compounds described in International Patent Application Publication (WO 2005/085216), International Patent Application Publication (WO 2007/026965), International Patent Application Publication (WO 2007/105814), Japanese Patent Application Publication (JP 2007/016017), Japanese Patent Application Publication (JP 2007/106756), Japanese Patent Application Publication (JP 2007/308471) and the like.

In each of the reactions, each of the production intermediates to be the starting materials of Production Method A to Production Method K can be obtained by common after treatment after the completion of the reaction.

Furthermore, each of the production intermediates produced by these methods may be used as it is without isolation and purification in a reaction of the next process.

Specific examples of the active compounds represented by Structure Formulae [1]-1 to [1]-110 and [2]-1 to [2]-75 included in the present invention include compounds shown in Table 3 to Table 5. However, the compounds in Table 3 to Table 5 are only for exemplification and the present invention is not limited to these compounds.

TABLE 3

Compounds represented by Structure Formulae [1]-1 to [1]-110 and [2]-1 to [2]-75 having structures in which G² is represented by G²-1-a or G²-1-b.

In Table, the number representing the substitution site of a substituent (X)_(m) corresponds to the site indicated by the number in each of Structure Formulae [1]-1 to [1]-110 and [2]-1 to [2]-75.

Furthermore, in Table, aromatic heterocyclic rings represented by D8-1a to D35-1c represent the following structures,

for example, the expression (CH₂(D8-3b)Cl) represents a 3-chloro-1-methylpyrazol-5-ylmethyl group and the expression ((D34-1c)Cl) represents a 5-chloropyrimidin-2-yl group,

in Table, aliphatic heterocyclic rings represented by E4-1a to E7-1b represent the following structures,

for example, the expression (CH₂(E7-1a)) represents a 1,3-dioxolan-2-ylmethyl group and the expression (CH₂(E7-1b)CH₃) represents a 2-methyl-1,3-dioxolan-2-ylmethyl group.

Furthermore, in Table, T-2 and T-3 represent the following structures,

in Table, the description of Et represents an ethyl group and, in the same manner, n-Pr and Pr-n represent normal propyl groups, i-Pr and Pr-i represent isopropyl groups, c-Pr and Pr-c represent cyclopropyl groups, t-Bu and Bu-t represent tertiary butyl groups, c-Bu and Bu-c represent cyclobutyl groups, and Ph represents a phenyl group.

TABLE 4 (X)_(m) R³ R² R¹ 3-Cl CF₃ H CH₂C(O)NHCH₂CF₃ 3-Cl CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Cl CF₃ H CH₂(D10-2a) 3-Cl CF₃ H CH═NOCH₃(Z) 3-Cl CF₃ H CH═NOEt(Z) 3-Br CF₃ C(O)OCH₃ CH₂OEt 3-Br CF₃ H CH₂OCH₂CF₃ 3-Br CF₃ H E4-1a 3-Br CF₃ H CH₂C(O)NHCH₂CF₃ 3-Br CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Br CF₃ H CH₂(D10-2a) 3-Br CF₃ H CH═NOCH₃(Z) 3-Br CF₃ H CH═NOEt(Z) 3-Br CF₃ C(O)Et C(O)OCH₃ 3-Br CF₃ H (D34-1c)CN 3-I CF₃ C(O)OCH₃ CH₂OEt 3-I CF₃ H CH₂OCH₂CF₃ 3-I CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3-I CF₃ H E4-1a 3-I CF₃ H CH₂C(O)NHCH₂CF₃ 3-I CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3-I CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-I CF₃ H CH₂(D10-2a) 3-I CF₃ H CH₂(D32-1a) 3-I CF₃ C(O)CH₃ CH₂(D32-1a) 3-I CF₃ C(O)OCH₃ CH₂(D32-1a) 3-I CF₃ H CH═NOCH₃(Z) 3-I CF₃ H CH═NOEt(Z) 3-I CF₃ C(O)Et C(O)OCH₃ 3-I CF₃ C(O)CH₃ (D34-1c)Cl 3-I CF₃ C(O)OCH₃ (D34-1c)Cl 3-I CF₃ H (D34-1c)CN 3-I CF₃ CH₃ (D34-1c)CN 3-I CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3-I CF₃ C(O)Pr-i (D34-1c)CN 3-I CF₂Cl H CH₂C(O)NHCH₂CF₃ 3-I CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3-I CF₂Cl H CH₂(D10-2a) 3-I CF₂Cl H CH═NOCH₃(Z) 3-I CF₂Cl H CH═NOEt(Z) 3-CF₃ CF₃ C(O)OCH₃ CH₂OEt 3-CF₃ CF₃ H CH₂OCH₂CF₃ 3-CF₃ CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3-CF₃ CF₃ H E4-1a 3-CF₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3-CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3-CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-CF₃ CF₃ H CH₂(D10-2a) 3-CF₃ CF₃ H CH₂(D32-1a) 3-CF₃ CF₃ C(O)CH₃ CH₂(D32-1a) 3-CF₃ CF₃ C(O)OCH₃ CH₂(D32-1a) 3-CF₃ CF₃ H CH═NOCH₃(Z) 3-CF₃ CF₃ H CH═NOEt(Z) 3-CF₃ CF₃ C(O)Et C(O)OCH₃ 3-CF₃ CF₃ C(O)CH₃ (D34-1c)Cl 3-CF₃ CF₃ C(O)OCH₃ (D34-1c)Cl 3-CF₃ CF₃ H (D34-1c)CN 3-CF₃ CF₃ CH₃ (D34-1c)CN 3-CF₃ CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3-CF₃ CF₃ C(O)Pr-i (D34-1c)CN 3-CF₃ CF₂Cl H CH₂C(O)NHCH₂CF₃ 3-CF₃ CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3-CF₃ CF₂Cl H CH₂(D10-2a) 3-CF₃ CF₂Cl H CH═NOCH₃(Z) 3-CF₃ CF₂Cl H CH═NOEt(Z) 3-CF₂CF₃ CF₃ C(O)OCH₃ CH₂OEt 3-CF₂CF₃ CF₃ H CH₂OCH₂CF₃ 3-CF₂CF₃ CF₃ H E4-1a 3-CF₂CF₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3-CF₂CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-CF₂CF₃ CF₃ H CH₂(D10-2a) 3-CF₂CF₃ CF₃ H CH═NOCH₃(Z) 3-CF₂CF₃ CF₃ H CH═NOEt(Z) 3-CF₂CF₃ CF₃ C(O)Et C(O)OCH₃ 3-CF₂CF₃ CF₃ H (D34-1c)CN 3-CF₂CF₂CF₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3-CF₂CF₂CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-CF₂CF₂CF₃ CF₃ H CH₂(D10-2a) 3-CF₂CF₂CF₃ CF₃ H CH═NOCH₃(Z) 3-CF₂CF₂CF₃ CF₃ H CH═NOEt(Z) 3-CF(CF₃)₂ CF₃ H CH₂C(O)NHCH₂CF₃ 3-CF(CF₃)₂ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-CF(CF₃)₂ CF₃ H CH₂(D10-2a) 3-CF(CF₃)₂ CF₃ H CH═NOCH₃(Z) 3-CF(CF₃)₂ CF₃ H CH═NOEt(Z) 3-OCF₃ CF₃ C(O)OCH₃ CH₂OEt 3-OCF₃ CF₃ H CH₂OCH₂CF₃ 3-OCF₃ CF₃ H E4-1a 3-OCF₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3-OCF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-OCF₃ CF₃ H CH₂(D10-2a) 3-OCF₃ CF₃ H CH═NOCH₃(Z) 3-OCF₃ CF₃ H CH═NOEt(Z) 3-OCF₃ CF₃ C(O)Et C(O)OCH₃ 3-OCF₃ CF₃ H (D34-1c)CN 3-OCF₂Br CF₃ H CH₂C(O)NHCH₂CF₃ 3-OCF₂Br CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-OCF₂Br CF₃ H CH₂(D10-2a) 3-OCF₂Br CF₃ H CH═NOCH₃(Z) 3-OCF₂Br CF₃ H CH═NOEt(Z) 3-SCF₃ CF₃ C(O)OCH₃ CH₂OEt 3-SCF₃ CF₃ H CH₂OCH₂CF₃ 3-SCF₃ CF₃ H E4-1a 3-SCF₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3-SCF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-SCF₃ CF₃ H CH₂(D10-2a) 3-SCF₃ CF₃ H CH═NOCH₃(Z) 3-SCF₃ CF₃ H CH═NOEt(Z) 3-SCF₃ CF₃ C(O)Et C(O)OCH₃ 3-SCF₃ CF₃ H (D34-1c)CN 3-SCF₂Cl CF₃ H CH₂C(O)NHCH₂CF₃ 3-SCF₂Cl CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-SCF₂Cl CF₃ H CH₂(D10-2a) 3-SCF₂Cl CF₃ H CH═NOCH₃(Z) 3-SCF₂Cl CF₃ H CH═NOEt(Z) 3-SCF₂Br CF₃ H CH₂C(O)NHCH₂CF₃ 3-SCF₂Br CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-SCF₂Br CF₃ H CH₂(D10-2a) 3-SCF₂Br CF₃ H CH═NOCH₃(Z) 3-SCF₂Br CF₃ H CH═NOEt(Z) 3-SF₅ CF₃ C(O)OCH₃ CH₂OEt 3-SF₅ CF₃ H CH₂OCH₂CF₃ 3-SF₅ CF₃ H E4-1a 3-SF₅ CF₃ H CH₂C(O)NHCH₂CF₃ 3-SF₅ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-SF₅ CF₃ H CH₂(D10-2a) 3-SF₅ CF₃ H CH═NOCH₃(Z) 3-SF₅ CF₃ H CH═NOEt(Z) 3-SF₅ CF₃ C(O)Et C(O)OCH₃ 3-SF₅ CF₃ H (D34-1c)CN 3-Cl-4-F CF₃ C(O)OCH₃ CH₂OEt 3-Cl-4-F CF₃ H CH₂OCH₂CF₃ 3-Cl-4-F CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3-Cl-4-F CF₃ H E4-1a 3-Cl-4-F CF₃ H CH₂C(O)NHCH₂CF₃ 3-Cl-4-F CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3-Cl-4-F CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Cl-4-F CF₃ H CH₂(D10-2a) 3-Cl-4-F CF₃ H CH₂(D32-1a) 3-Cl-4-F CF₃ C(O)CH₃ CH₂(D32-1a) 3-Cl-4-F CF₃ C(O)OCH₃ CH₂(D32-1a) 3-Cl-4-F CF₃ H CH═NOCH₃(Z) 3-Cl-4-F CF₃ H CH═NOEt(Z) 3-Cl-4-F CF₃ C(O)Et C(O)OCH₃ 3-Cl-4-F CF₃ C(O)CH₃ (D34-1c)Cl 3-Cl-4-F CF₃ C(O)OCH₃ (D34-1c)Cl 3-Cl-4-F CF₃ H (D34-1c)CN 3-Cl-4-F CF₃ CH₃ (D34-1c)CN 3-Cl-4-F CF₃ CH₂OC(O)OH₃ (D34-1c)CN 3-Cl-4-F CF₃ C(O)Pr-i (D34-1c)CN 3-Cl-4-F CF₂Cl H CH₂C(O)NHCH₂CF₃ 3-Cl-4-F CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Cl-4-F CF₂Cl H CH₂(D10-2a) 3-Cl-4-F CF₂Cl H CH═NOCH₃(Z) 3-Cl-4-F CF₂Cl H CH═NOEt(Z) 3-F-5-Cl CF₃ C(O)OCH₃ CH₂OEt 3-F-5-Cl CF₃ H CH₂OCH₂CF₃ 3-F-5-Cl CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3-F-5-Cl CF₃ H E4-1a 3-F-5-Cl CF₃ H CH₂C(O)NHCH₂CF₃ 3-F-5-Cl CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3-F-5-Cl CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-F-5-Cl CF₃ H CH₂(D10-2a) 3-F-5-Cl CF₃ H CH₂(D32-1a) 3-F-5-Cl CF₃ C(O)CH₃ CH₂(D32-1a) 3-F-5-Cl CF₃ C(O)OCH₃ CH₂(D32-1a) 3-F-5-Cl CF₃ H CH═NOCH₃(Z) 3-F-5-Cl CF₃ H CH═NOEt(Z) 3-F-5-Cl CF₃ C(O)Et C(O)OCH₃ 3-F-5-Cl CF₃ C(O)CH₃ (D34-1c)Cl 3-F-5-Cl CF₃ C(O)OCH₃ (D34-1c)Cl 3-F-5-Cl CF₃ H (D34-1c)CN 3-F-5-Cl CF₃ CH₃ (D34-1c)CN 3-F-5-Cl CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3-F-5-Cl CF₃ C(O)Pr-i (D34-1c)CN 3-F-5-Cl CF₂Cl H CH₂C(O)NHCH₂CF₃ 3-F-5-Cl CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3-F-5-Cl CF₂Cl H CH₂(D10-2a) 3-F-5-Cl CF₂Cl H CH═NOCH₃(Z) 3-F-5-Cl CF₂Cl H CH═NOEt(Z) 3,4-Cl₂ CF₃ C(O)OCH₃ CH₂OEt 3,4-Cl₂ CF₃ H CH₂OCH₂CF₃ 3,4-Cl₂ CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3,4-Cl₂ CF₃ H E4-1a 3,4-Cl₂ CF₃ H CH₂C(O)NHCH₂CF₃ 3,4-Cl₂ CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3,4-Cl₂ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3,4-Cl₂ CF₃ H CH₂(D10-2a) 3,4-Cl₂ CF₃ H CH₂(D32-1a) 3,4-Cl₂ CF₃ C(O)CH₃ CH₃(D32-1a) 3,4-Cl₂ CF₃ C(O)OCH₃ CH₂(D32-1a) 3,4-Cl₂ CF₃ H CH═NOCH₃(Z) 3,4-Cl₂ CF₃ H CH═NOEt(Z) 3,4-Cl₂ CF₃ C(O)Et C(O)OCH₃ 3,4-Cl₂ CF₃ C(O)CH₃ (D34-1c)Cl 3,4-Cl₂ CF₃ C(O)OCH₃ (D34-1c)Cl 3,4-Cl₂ CF₃ H (D34-1c)CN 3,4-Cl₂ CF₃ CH₃ (D34-1c)CN 3,4-Cl₂ CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3,4-Cl₂ CF₃ C(O)Pr-i (D34-1c)CN 3,4-Cl₂ CF₂Cl H CH₂C(O)NHCH₂CF₃ 3,4-Cl₂ CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3,4-Cl₂ CF₂Cl H CH₂(D10-2a) 3,4-Cl₂ CF₂Cl H CH═NOCH₃(Z) 3,4-Cl₂ CF₂Cl H CH═NOEt(Z) 3,5-Cl₂ CF₃ C(O)CH₃ CH₂CF₃ 3,5-Cl₂ CF₃ C(O)OCH₃ CH₂OCH₃ 3,5-Cl₂ CF₃ C(O)OCH₃ CH₂OEt 3,5-Cl₂ CF₃ C(O)OCH₃ CH₂OPr-i 3,5-Cl₂ CF₃ H CH₂OCH₂CF₃ 3,5-Cl₂ CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3,5-Cl₂ CF₃ H E4-1a 3,5-Cl₂ CF₃ H CH₂C(O)NHCH₂CH₂Cl 3,5-Cl₂ CF₃ H CH₂C(O)NHCH₂CF₃ 3,5-Cl₂ CF₃ H CH(CH₃)C(O)NHCH₂CH₂Cl 3,5-Cl₂ CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3,5-Cl₂ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3,5-Cl₂ CF₃ H CH₂(D10-2a) 3,5-Cl₂ CF₃ C(O)CH₃ CH₂(D10-2a) 3,5-Cl₂ CF₃ C(O)Et CH₂(D10-2a) 3,5-Cl₂ CF₃ H CH₂(D32-1a) 3,5-Cl₂ CF₃ C(O)CH₃ CH₂(D32-1a) 3,5-Cl₂ CF₃ C(O)Et CH₂(D32-1a) 3,5-Cl₂ CF₃ C(O)OCH₃ CH₂(D32-1a) 3,5-Cl₂ CF₃ H CH═NOCH₃(Z) 3,5-Cl₂ CF₃ CH₂OCH₃ CH═NOCH₃ 3,5-Cl₂ CF₃ CH₂OC(O)CH₃ CH═NOCH₃ 3,5-Cl₂ CF₃ H CH═NOEt(Z) 3,5-Cl₂ CF₃ C(O)Et C(O)OCH₃ 3,5-Cl₂ CF₃ CH₃ (D34-1c)Cl 3,5-Cl₂ CF₃ CH₂OC(O)CH₃ (D34-1c)Cl 3,5-Cl₂ CF₃ C(O)CH₃ (D34-1c)Cl 3,5-Cl₂ CF₃ C(O)Pr-c (D34-1c)Cl 3,5-Cl₂ CF₃ C(O)CH₂OCH₃ (D34-1c)Cl 3,5-Cl₂ CF₃ C(O)OCH₃ (D34-1c)Cl 3,5-Cl₂ CF₃ C(O)OCH₂Cl (D34-1c)Cl 3,5-Cl₂ CF₃ C(O)OCH₂CH₂OCH₃ (D34-1c)Cl 3,5-Cl₂ CF₃ H (D34-1c)CN 3,5-Cl₂ CF₃ CH₃ (D34-1c)CN 3,5-Cl₂ CF₃ CH₂OCH₃ (D34-1c)CN 3,5-Cl₂ CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3,5-Cl₂ CF₃ C(O)CH₃ (D34-1c)CN 3,5-Cl₂ CF₃ C(O)Pr-i (D34-1c)CN 3,5-Cl₂ CF₃ C(O)OCH₃ (D34-1c)CN 3,5-Cl₂ CF₃ H D34-3a 3,5-Cl₂ CF₃ CH₃ D34-3a 3,5-Cl₂ CF₃ CH₂OCH₃ D34-3a 3,5-Cl₂ CF₃ C(O)Et D34-3a 3,5-Cl₂ CF₃ C(O)Pr-i D34-3a 3,5-Cl₂ CF₃ C(O)OCH₃ (D35-1c)Cl 3,5-Cl₂ CF₃ H N(CH₃)Ph 3,5-Cl₂ CF₃ H N(CH₃)(D34-1a) 3,5-Cl₂ CF₂Cl C(O)OCH₃ CH₂OEt 3,5-Cl₂ CF₂Cl H CH₂OCH₂CF₃ 3,5-Cl₂ CF₂Cl H E4-1a 3,5-Cl₂ CF₂Cl H CH₂C(O)NHCH₂CF₃ 3,5-Cl₂ CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3,5-Cl₂ CF₂Cl H CH₂(D10-2a) 3,5-Cl₂ CF₂Cl H CH═NOCH₃(Z) 3,5-Cl₂ CF₂Cl H CH═NOEt(Z) 3,5-Cl₂ CF₂Cl C(O)Et C(O)OCH₃ 3,5-Cl₂ CF₂Cl H (D34-1c)CN 3-Br-4-F CF₃ C(O)OCH₃ CH₂OEt 3-Br-4-F CF₃ H CH₂OCH₂CF₃ 3-Br-4-F CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3-Br-4-F CF₃ H E4-1a 3-Br-4-F CF₃ H CH₂C(O)NHCH₂CF₃ 3-Br-4-F CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3-Br-4-F CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Br-4-F CF₃ H CH₂(D10-2a) 3-Br-4-F CF₃ H CH₂(D32-1a) 3-Br-4-F CF₃ C(O)CH₃ CH₂(D32-1a) 3-Br-4-F CF₃ C(O)OCH₃ CH₂(D32-1a) 3-Br-4-F CF₃ H CH═NOCH₃(Z) 3-Br-4-F CF₃ H CH═NOEt(Z) 3-Br-4-F CF₃ C(O)Et C(O)OCH₃ 3-Br-4-F CF₃ C(O)CH₃ (D34-1c)Cl 3-Br-4-F CF₃ C(O)OCH₃ (D34-1c)Cl 3-Br-4-F CF₃ H (D34-1c)CN 3-Br-4-F CF₃ CH₃ (D34-1c)CN 3-Br-4-F CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3-Br-4-F CF₃ C(O)Pr-i (D34-1c)CN 3-Br-4-F CF₂Cl H CH₂C(O)NHCH₂CF₃ 3-Br-4-F CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Br-4-F CF₂Cl H CH₂(D10-2a) 3-Br-4-F CF₂Cl H CH═NOCH₃(Z) 3-Br-4-F CF₂Cl H CH═NOEt(Z) 3-F-5-Br CF₃ C(O)OCH₃ CH₂OEt 3-F-5-Br CF₃ H CH₂OCH₂CF₃ 3-F-5-Br CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3-F-5-Br CF₃ H E4-1a 3-F-5-Br CF₃ H CH₂C(O)NHCH₂CF₃ 3-F-5-Br CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3-F-5-Br CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-F-5-Br CF₃ H CH₂(D10-2a) 3-F-5-Br CF₃ H CH₂(D32-1a) 3-F-5-Br CF₃ C(O)CH₃ CH₂(D32-1a) 3-F-5-Br CF₃ C(O)OCH₃ CH₂(D32-1a) 3-F-5-Br CF₃ H CH═NOCH₃(Z) 3-F-5-Br CF₃ H CH═NOEt(Z) 3-F-5-Br CF₃ C(O)Et C(O)OCH₃ 3-F-5-Br CF₃ C(O)CH₃ (D34-1c)Cl 3-F-5-Br CF₃ C(O)OCH₃ (D34-1c)Cl 3-F-5-Br CF₃ H (D34-1c)CN 3-F-5-Br CF₃ CH₃ (D34-1c)CN 3-F-5-Br CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3-F-5-Br CF₃ C(O)Pr-i (D34-1c)CN 3-F-5-Br CF₂Cl H CH₂C(O)NHCH₂CF₃ 3-F-5-Br CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3-F-5-Br CF₂Cl H CH₂(D10-2a) 3-F-5-Br CF₂Cl H CH═NOCH₃(Z) 3-F-5-Br CF₂Cl H CH═NOEt(Z) 3-Br-4-Cl CF₃ C(O)OCH₃ CH₂OEt 3-Br-4-Cl CF₃ H CH₂OCH₂CF₃ 3-Br-4-Cl CF₃ H E4-1a 3-Br-4-Cl CF₃ H CH₂C(O)NHCH₂CF₃ 3-Br-4-Cl CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Br-4-Cl CF₃ H CH₂(D10-2a) 3-Br-4-Cl CF₃ H CH═NOCH₃(Z) 3-Br-4-Cl CF₃ H CH═NOEt(Z) 3-Br-4-Cl CF₃ C(O)Et C(O)OCH₃ 3-Br-4-Cl CF₃ H (D34-1c)CN 3-Cl-4-Br CF₃ C(O)OCH₃ CH₂OEt 3-Cl-4-Br CF₃ H CH₂OCH₂CF₃ 3-Cl-4-Br CF₃ H E4-1a 3-Cl-4-Br CF₃ H CH₂C(O)NHCH₂CF₃ 3-Cl-4-Br CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Cl-4-Br CF₃ H CH₂(D10-2a) 3-Cl-4-Br CF₃ H CH═NOCH₃(Z) 3-Cl-4-Br CF₃ H CH═NOEt(Z) 3-Cl-4-Br CF₃ C(O)Et C(O)OCH₃ 3-Cl-4-Br CF₃ H (D34-1c)CN 3-Cl-5-Br CF₃ C(O)CH₃ CH₂CF₃ 3-Cl-5-Br CF₃ C(O)OCH₃ CH₂OCH₃ 3-Cl-5-Br CF₃ C(O)OCH₃ CH₂OEt 3-Cl-5-Br CF₃ C(O)OCH₃ CH₂OPr-i 3-Cl-5-Br CF₃ H CH₂OCH₂CF₃ 3-Cl-5-Br CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3-Cl-5-Br CF₃ H E4-1a 3-Cl-5-Br CF₃ H CH₂C(O)NHCH₂CH₂Cl 3-Cl-5-Br CF₃ H CH₂C(O)NHCH₂CF₃ 3-Cl-5-Br CF₃ H CH(CH₃)C(O)NHCH₂CH₂Cl 3-Cl-5-Br CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3-Cl-5-Br CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Cl-5-Br CF₃ H CH₂(D10-2a) 3-Cl-5-Br CF₃ C(O)CH₃ CH₂(D10-2a) 3-Cl-5-Br CF₃ C(O)Et CH₂(D10-2a) 3-Cl-5-Br CF₃ H CH₂(D32-1a) 3-Cl-5-Br CF₃ C(O)CH₃ CH₂(D32-1a) 3-Cl-5-Br CF₃ C(O)Et CH₂(D32-1a) 3-Cl-5-Br CF₃ C(O)OCH₃ CH₂(D32-1a) 3-Cl-5-Br CF₃ H CH═NOCH₃(Z) 3-Cl-5-Br CF₃ CH₂OCH₃ CH═NOCH₃ 3-Cl-5-Br CF₃ CH₂OC(O)CH₃ CH═NOCH₃ 3-Cl-5-Br CF₃ H CH═NOEt(Z) 3-Cl-5-Br CF₃ C(O)Et C(O)OCH₃ 3-Cl-5-Br CF₃ CH₂OC(O)CH₃ (D34-1c)Cl 3-Cl-5-Br CF₃ C(O)CH₃ (D34-1c)Cl 3-Cl-5-Br CF₃ C(O)Pr-c (D34-1c)Cl 3-Cl-5-Br CF₃ C(O)OCH₃ (D34-1c)Cl 3-Cl-5-Br CF₃ H (D34-1c)CN 3-Cl-5-Br CF₃ CH₃ (D34-1c)CN 3-Cl-5-Br CF₃ CH₂OCH₃ (D34-1c)CN 3-Cl-5-Br CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3-Cl-5-Br CF₃ C(O)Pr-i (D34-1c)CN 3-Cl-5-Br CF₃ C(O)OCH₃ (D34-1c)CN 3-Cl-5-Br CF₃ CH₂OCH₃ D34-3a 3-Cl-5-Br CF₃ C(O)Et D34-3a 3-Cl-5-Br CF₃ C(O)Pr-i D34-3a 3-Cl-5-Br CF₃ C(O)OCH₃ (D35-1c)Cl 3-Cl-5-Br CF₃ H N(CH₃)Ph 3-Cl-5-Br CF₃ H N(CH₃)(D34-1a) 3-Cl-5-Br CF₂Cl C(O)OCH₃ CH₂OEt 3-Cl-5-Br CF₂Cl H CH₂OCH₂CF₃ 3-Cl-5-Br CF₂Cl H E4-1a 3-Cl-5-Br CF₂Cl H CH₂C(O)NHCH₂CF₃ 3-Cl-5-Br CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Cl-5-Br CF₂Cl H CH₂(D10-2a) 3-Cl-5-Br CF₂Cl H CH═NOCH₃(Z) 3-Cl-5-Br CF₂Cl H CH═NOEt(Z) 3-Cl-5-Br CF₂Cl C(O)Et C(O)OCH₃ 3-Cl-5-Br CF₂Cl H (D34-1c)CN 3,4-Br₂ CF₃ C(O)OCH₃ CH₂OEt 3,4-Br₂ CF₃ H CH₂OCH₂CF₃ 3,4-Br₂ CF₃ H E4-1a 3,4-Br₂ CF₃ H CH₂C(O)NHCH₂CF₃ 3,4-Br₂ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3,4-Br₂ CF₃ H CH₂(D10-2a) 3,4-Br₂ CF₃ H CH═NOCH₃(Z) 3,4-Br₂ CF₃ H CH═NOEt(Z) 3,4-Br₂ CF₃ C(O)Et C(O)OCH₃ 3,4-Br₂ CF₃ H (D34-1c)CN 3,5-Br₂ CF₃ C(O)CH₃ CH₂CF₃ 3,5-Br₂ CF₃ C(O)OCH₃ CH₂OCH₃ 3,5-Br₂ CF₃ C(O)OCH₃ CH₂OEt 3,5-Br₂ CF₃ C(O)OCH₃ CH₂OPr-i 3,5-Br₂ CF₃ H CH₂OCH₂CF₃ 3,5-Br₂ CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3,5-Br₂ CF₃ H E4-1a 3,5-Br₂ CF₃ H CH₂C(O)NHCH₂CH₂Cl 3,5-Br₂ CF₃ H CH₂C(O)NHCH₂CF₃ 3,5-Br₂ CF₃ H CH(CH₃)C(O)NHCH₂CH₂Cl 3,5-Br₂ CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3,5-Br₂ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3,5-Br₂ CF₃ H CH₂(D10-2a) 3,5-Br₂ CF₃ C(O)CH₃ CH₂(D10-2a) 3,5-Br₂ CF₃ C(O)Et CH₂(D10-2a) 3,5-Br₂ CF₃ H CH₂(D32-1a) 3,5-Br₂ CF₃ C(O)CH₃ CH₃(D32-1a) 3,5-Br₂ CF₃ C(O)Et CH₂(D32-1a) 3,5-Br₂ CF₃ C(O)OCH₃ CH₂(D32-1a) 3,5-Br₂ CF₃ H CH═NOCH₃(Z) 3,5-Br₂ CF₃ CH₂OCH₃ CH═NOCH₃ 3,5-Br₂ CF₃ CH₂OC(O)CH₃ CH═NOCH₃ 3,5-Br₂ CF₃ H CH═NOEt(Z) 3,5-Br₂ CF₃ C(O)Et C(O)OCH₃ 3,5-Br₂ CF₃ CH₂OC(O)CH₃ (D34-1c)Cl 3,5-Br₂ CF₃ C(O)CH₃ (D34-1c)Cl 3,5-Br₂ CF₃ C(O)Pr-c (D34-1c)Cl 3,5-Br₂ CF₃ C(O)OCH₃ (D34-1c)Cl 3,5-Br₂ CF₃ H (D34-1c)CN 3,5-Br₂ CF₃ CH₃ (D34-1c)CN 3,5-Br₂ CF₃ CH₂OCH₃ (D34-1c)CN 3,5-Br₂ CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3,5-Br₂ CF₃ C(O)Pr-i (D34-1c)CN 3,5-Br₂ CF₃ C(O)OCH₃ (D34-1c)CN 3,5-Br₂ CF₃ CH₂OCH₃ D34-3a 3,5-Br₂ CF₃ C(O)Et D34-3a 3,5-Br₂ CF₃ C(O)Pr-i D34-3a 3,5-Br₂ CF₃ C(O)OCH₃ (D35-1c)Cl 3,5-Br₂ CF₃ H N(CH₃)Ph 3,5-Br₂ CF₃ H N(CH₃)(D34-1a) 3,5-Br₂ CF₂Cl C(O)OCH₃ CH₂OEt 3,5-Br₂ CF₂Cl H CH₂OCH₂CF₃ 3,5-Br₂ CF₂Cl H E4-1a 3,5-Br₂ CF₂Cl H CH₂C(O)NHCH₂CF₃ 3,5-Br₂ CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3,5-Br₂ CF₂Cl H CH₂(D10-2a) 3,5-Br₂ CF₂Cl H CH═NOCH₃(Z) 3,5-Br₂ CF₂Cl H CH═NOEt(Z) 3,5-Br₂ CF₂Cl C(O)Et C(O)OCH₃ 3,5-Br₂ CF₂Cl H (D34-1c)CN 3-I-4-F CF₃ C(O)OCH₃ CH₂OEt 3-I-4-F CF₃ H CH₂OCH₂CF₃ 3-I-4-F CF₃ H E4-1a 3-I-4-F CF₃ H CH₂C(O)NHCH₂CF₃ 3-I-4-F CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-I-4-F CF₃ H CH₂(D10-2a) 3-I-4-F CF₃ H CH═NOCH₃(Z) 3-I-4-F CF₃ H CH═NOEt(Z) 3-I-4-F CF₃ C(O)Et C(O)OCH₃ 3-I-4-F CF₃ H (D34-1c)CN 3-F-5-I CF₃ C(O)OCH₃ CH₂OEt 3-F-5-I CF₃ H CH₂OCH₂CF₃ 3-F-5-I CF₃ H E4-1a 3-F-5-I CF₃ H CH₂C(O)NHCH₂CF₃ 3-F-5-I CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-F-5-I CF₃ H CH₂(D10-2a) 3-F-5-I CF₃ H CH═NOCH₃(Z) 3-F-5-I CF₃ H CH═NOEt(Z) 3-F-5-I CF₃ C(O)Et C(O)OCH₃ 3-F-5-I CF₃ H (D34-1c)CN 3-Cl-5-I CF₃ C(O)OCH₃ CH₂OEt 3-Cl-5-I CF₃ H CH₂OCH₂CF₃ 3-Cl-5-I CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3-Cl-5-I CF₃ H E4-1a 3-Cl-5-I CF₃ H CH₂C(O)NHCH₂CF₃ 3-Cl-5-I CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3-Cl-5-I CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Cl-5-I CF₃ H CH₂(D10-2a) 3-Cl-5-I CF₃ H CH₂(D32-1a) 3-Cl-5-I CF₃ C(O)CH₃ CH₂(D32-1a) 3-Cl-5-I CF₃ C(O)OCH₃ CH₂(D32-1a) 3-Cl-5-I CF₃ H CH═NOCH₃(Z) 3-Cl-5-I CF₃ H CH═NOEt(Z) 3-Cl-5-I CF₃ C(O)Et C(O)OCH₃ 3-Cl-5-I CF₃ C(O)CH₃ (D34-1c)Cl 3-Cl-5-I CF₃ C(O)OCH₃ (D34-1c)Cl 3-Cl-5-I CF₃ H (D34-1c)CN 3-Cl-5-I CF₃ CH₃ (D34-1c)CN 3-Cl-5-I CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3-Cl-5-I CF₃ C(O)Pr-i (D34-1c)CN 3-Cl-5-I CF₂Cl H CH₂C(O)NHCH₂CF₃ 3-Cl-5-I CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Cl-5-I CF₂Cl H CH₂(D10-2a) 3-Cl-5-I CF₂Cl H CH═NOCH₃(Z) 3-Cl-5-I CF₂Cl H CH═NOEt(Z) 3-Cl-5-CH₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3-Cl-5-CH₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Cl-5-CH₃ CF₃ H CH₂(D10-2a) 3-Cl-5-CH₃ CF₃ H CH═NOCH₃(Z) 3-Cl-5-CH₃ CF₃ H CH═NOEt(Z) 3-Br-5-CH₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3-Br-5-CH₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Br-5-CH₃ CF₃ H CH₂(D10-2a) 3-Br-5-CH₃ CF₃ H CH═NOCH₃(Z) 3-Br-5-CH₃ CF₃ H CH═NOEt(Z) 3-CF₃-4-F CF₃ C(O)OCH₃ CH₂OEt 3-CF₃-4-F CF₃ H CH₂OCH₂CF₃ 3-CF₃-4-F CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3-CF₃-4-F CF₃ H E4-1a 3-CF₃-4-F CF₃ H CH₂C(O)NHCH₂CF₃ 3-CF₃-4-F CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3-CF₃-4-F CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-CF₃-4-F CF₃ H CH₂(D10-2a) 3-CF₃-4-F CF₃ H CH₂(D32-1a) 3-CF₃-4-F CF₃ C(O)CH₃ CH₂(D32-1a) 3-CF₃-4-F CF₃ C(O)OCH₃ CH₂(D32-1a) 3-CF₃-4-F CF₃ H CH═NOCH₃(Z) 3-CF₃-4-F CF₃ H CH═NOEt(Z) 3-CF₃-4-F CF₃ C(O)Et C(O)OCH₃ 3-CF₃-4-F CF₃ C(O)CH₃ (D34-1c)Cl 3-CF₃-4-F CF₃ C(O)OCH₃ (D34-1c)Cl 3-CF₃-4-F CF₃ H (D34-1c)CN 3-CF₃-4-F CF₃ CH₃ (D34-1c)CN 3-CF₃-4-F CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3-CF₃-4-F CF₃ C(O)Pr-i (D34-1c)CN 3-CF₃-4-F CF₂Cl H CH₂C(O)NHCH₂CF₃ 3-CF₃-4-F CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3-CF₃-4-F CF₂Cl H CH₂(D10-2a) 3-CF₃-4-F CF₂Cl H CH═NOCH₃(Z) 3-CF₃-4-F CF₂Cl H CH═NOEt(Z) 3-F-5-CF₃ CF₃ C(O)OCH₃ CH₂OEt 3-F-5-CF₃ CF₃ H CH₂OCH₂CF₃ 3-F-5-CF₃ CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3-F-5-CF₃ CF₃ H E4-1a 3-F-5-CF₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3-F-5-CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3-F-5-CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-F-5-CF₃ CF₃ H CH₂(D10-2a) 3-F-5-CF₃ CF₃ H CH₂(D32-1a) 3-F-5-CF₃ CF₃ C(O)CH₃ CH₂(D32-1a) 3-F-5-CF₃ CF₃ C(O)OCH₃ CH₂(D32-1a) 3-F-5-CF₃ CF₃ H CH═NOCH₃(Z) 3-F-5-CF₃ CF₃ H CH═NOEt(Z) 3-F-5-CF₃ CF₃ C(O)Et C(O)OCH₃ 3-F-5-CF₃ CF₃ C(O)CH₃ (D34-1c)Cl 3-F-5-CF₃ CF₃ C(O)OCH₃ (D34-1c)Cl 3-F-5-CF₃ CF₃ H (D34-1c)CN 3-F-5-CF₃ CF₃ CH₃ (D34-1c)CN 3-F-5-CF₃ CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3-F-5-CF₃ CF₃ C(O)Pr-i (D34-1c)CN 3-F-5-CF₃ CF₂Cl H CH₂C(O)NHCH₂CF₃ 3-F-5-CF₃ CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3-F-5-CF₃ CF₂Cl H CH₂(D10-2a) 3-F-5-CF₃ CF₂Cl H CH═NOCH₃(Z) 3-F-5-CF₃ CF₂Cl H CH═NOEt(Z) 3-CF₃-4-Cl CF₃ C(O)OCH₃ CH₂OEt 3-CF₃-4-Cl CF₃ H CH₂OCH₂CF₃ 3-CF₃-4-Cl CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3-CF₃-4-Cl CF₃ H E4-1a 3-CF₃-4-Cl CF₃ H CH₂C(O)NHCH₂CF₃ 3-CF₃-4-Cl CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3-CF₃-4-Cl CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-CF₃-4-Cl CF₃ H CH₂(D10-2a) 3-CF₃-4-Cl CF₃ H CH₂(D32-1a) 3-CF₃-4-Cl CF₃ C(O)CH₃ CH₂(D32-1a) 3-CF₃-4-Cl CF₃ C(O)OCH₃ CH₂(D32-1a) 3-CF₃-4-Cl CF₃ H CH═NOCH₃(Z) 3-CF₃-4-Cl CF₃ H CH═NOEt(Z) 3-CF₃-4-Cl CF₃ C(O)Et C(O)OCH₃ 3-CF₃-4-Cl CF₃ C(O)CH₃ (D34-1c)Cl 3-CF₃-4-Cl CF₃ C(O)OCH₃ (D34-1c)Cl 3-CF₃-4-Cl CF₃ H (D34-1c)CN 3-CF₃-4-Cl CF₃ CH₃ (D34-1c)CN 3-CF₃-4-Cl CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3-CF₃-4-Cl CF₃ C(O)Pr-i (D34-1c)CN 3-CF₃-4-Cl CF₂Cl H CH₂C(O)NHCH₂CF₃ 3-CF₃-4-Cl CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3-CF₃-4-Cl CF₂Cl H CH₂(D10-2a) 3-CF₃-4-Cl CF₂Cl H CH═NOCH₃(Z) 3-CF₃-4-Cl CF₂Cl H CH═NOEt(Z) 3-Cl-5-CF₃ CF₃ C(O)CH₃ CH₂CF₃ 3-Cl-5-CF₃ CF₃ C(O)OCH₃ CH₂OCH₃ 3-Cl-5-CF₃ CF₃ C(O)OCH₃ CH₂OEt 3-Cl-5-CF₃ CF₃ C(O)OCH₃ CH₂OPr-i 3-Cl-5-CF₃ CF₃ H CH₂OCH₂CF₃ 3-Cl-5-CF₃ CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3-Cl-5-CF₃ CF₃ H E4-1a 3-Cl-5-CF₃ CF₃ H CH₂C(O)NHCH₂CH₂Cl 3-Cl-5-CF₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3-Cl-5-CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CH₂Cl 3-Cl-5-CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3-Cl-5-CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Cl-5-CF₃ CF₃ H CH₂(D10-2a) 3-Cl-5-CF₃ CF₃ C(O)CH₃ CH₂(D10-2a) 3-Cl-5-CF₃ CF₃ C(O)Et CH₂(D10-2a) 3-Cl-5-CF₃ CF₃ H CH₂(D32-1a) 3-Cl-5-CF₃ CF₃ C(O)CH₃ CH₂(D32-1a) 3-Cl-5-CF₃ CF₃ C(O)Et CH₂(D32-1a) 3-Cl-5-CF₃ CF₃ C(O)OCH₃ CH₂(D32-1a) 3-Cl-5-CF₃ CF₃ H CH═NOCH₃(Z) 3-Cl-5-CF₃ CF₃ CH₂OCH₃ CH═NOCH₃ 3-Cl-5-CF₃ CF₃ CH₂OC(O)CH₃ CH═NOCH₃ 3-Cl-5-CF₃ CF₃ H CH═NOEt(Z) 3-Cl-5-CF₃ CF₃ C(O)Et C(O)OCH₃ 3-Cl-5-CF₃ CF₃ CH₂OC(O)CH₃ (D34-1c)Cl 3-Cl-5-CF₃ CF₃ C(O)CH₃ (D34-1c)Cl 3-Cl-5-CF₃ CF₃ C(O)Pr-c (D34-1c)Cl 3-Cl-5-CF₃ CF₃ C(O)OCH₃ (D34-1c)Cl 3-Cl-5-CF₃ CF₃ H (D34-1c)CN 3-Cl-5-CF₃ CF₃ CH₃ (D34-1c)CN 3-Cl-5-CF₃ CF₃ CH₂OCH₃ (D34-1c)CN 3-Cl-5-CF₃ CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3-Cl-5-CF₃ CF₃ C(O)Pr-i (D34-1c)CN 3-Cl-5-CF₃ CF₃ C(O)OCH₃ (D34-1c)CN 3-Cl-5-CF₃ CF₃ CH₂OCH₃ D34-3a 3-Cl-5-CF₃ CF₃ C(O)Et D34-3a 3-Cl-5-CF₃ CF₃ C(O)Pr-i D34-3a 3-Cl-5-CF₃ CF₃ C(O)OCH₃ (D35-1c)Cl 3-Cl-5-CF₃ CF₃ H N(CH₃)Ph 3-Cl-5-CF₃ CF₃ H N(CH₃)(D34-1a) 3-Cl-5-CF₃ CF₂Cl C(O)OCH₃ CH₂OEt 3-Cl-5-CF₃ CF₂Cl H CH₂OCH₂CF₃ 3-Cl-5-CF₃ CF₂Cl H E4-1a 3-Cl-5-CF₃ CF₂Cl H CH₂C(O)NHCH₂CF₃ 3-Cl-5-CF₃ CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Cl-5-CF₃ CF₂Cl H CH₂(D10-2a) 3-Cl-5-CF₃ CF₂Cl H CH═NOCH₃(Z) 3-Cl-5-CF₃ CF₂Cl H CH═NOEt(Z) 3-Cl-5-CF₃ CF₂Cl C(O)Et C(O)OCH₃ 3-Cl-5-CF₃ CF₂Cl H (D34-1c)CN 3-Br-5-CF₃ CF₃ C(O)CH₃ CH₂CF₃ 3-Br-5-CF₃ CF₃ C(O)OCH₃ CH₂OCH₃ 3-Br-5-CF₃ CF₃ C(O)OCH₃ CH₂OEt 3-Br-5-CF₃ CF₃ C(O)OCH₃ CH₂OPr-i 3-Br-5-CF₃ CF₃ H CH₂OCH₂CF₃ 3-Br-5-CF₃ CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3-Br-5-CF₃ CF₃ H E4-1a 3-Br-5-CF₃ CF₃ H CH₂C(O)NHCH₂CH₂Cl 3-Br-5-CF₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3-Br-5-CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CH₂Cl 3-Br-5-CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3-Br-5-CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Br-5-CF₃ CF₃ H CH₂(D10-2a) 3-Br-5-CF₃ CF₃ C(O)CH₃ CH₂(D10-2a) 3-Br-5-CF₃ CF₃ C(O)Et CH₂(D10-2a) 3-Br-5-CF₃ CF₃ H CH₂(D32-1a) 3-Br-5-CF₃ CF₃ C(O)CH₃ CH₂(D32-1a) 3-Br-5-CF₃ CF₃ C(O)Et CH₂(D32-1a) 3-Br-5-CF₃ CF₃ C(O)OCH₃ CH₂(D32-1a) 3-Br-5-CF₃ CF₃ H CH═NOCH₃(Z) 3-Br-5-CF₃ CF₃ CH₂OCH₃ CH═NOCH₃ 3-Br-5-CF₃ CF₃ CH₂OC(O)CH₃ CH═NOCH₃ 3-Br-5-CF₃ CF₃ H CH═NOEt(Z) 3-Br-5-CF₃ CF₃ C(O)Et C(O)OCH₃ 3-Br-5-CF₃ CF₃ CH₂OC(O)CH₃ (D34-1c)Cl 3-Br-5-CF₃ CF₃ C(O)CH₃ (D34-1c)Cl 3-Br-5-CF₃ CF₃ C(O)Pr-c (D34-1c)Cl 3-Br-5-CF₃ CF₃ C(O)OCH₃ (D34-1c)Cl 3-Br-5-CF₃ CF₃ H (D34-1c)CN 3-Br-5-CF₃ CF₃ CH₃ (D34-1c)CN 3-Br-5-CF₃ CF₃ CH₂OCH₃ (D34-1c)CN 3-Br-5-CF₃ CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3-Br-5-CF₃ CF₃ C(O)Pr-i (D34-1c)CN 3-Br-5-CF₃ CF₃ C(O)OCH₃ (D34-1c)CN 3-Br-5-CF₃ CF₃ CH₂OCH₃ D34-3a 3-Br-5-CF₃ CF₃ C(O)Et D34-3a 3-Br-5-CF₃ CF₃ C(O)Pr-i D34-3a 3-Br-5-CF₃ CF₃ C(O)OCH₃ (D35-1c)Cl 3-Br-5-CF₃ CF₃ H N(CH₃)Ph 3-Br-5-CF₃ CF₃ H N(CH₃)(D34-1a) 3-Br-5-CF₃ CF₂Cl C(O)OCH₃ CH₂OEt 3-Br-5-CF₃ CF₂Cl H CH₂OCH₂CF₃ 3-Br-5-CF₃ CF₂Cl H E4-1a 3-Br-5-CF₃ CF₂Cl H CH₂C(O)NHCH₂CF₃ 3-Br-5-CF₃ CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Br-5-CF₃ CF₂Cl H CH₂(D10-2a) 3-Br-5-CF₃ CF₂Cl H CH═NOCH₃(Z) 3-Br-5-CF₃ CF₂Cl H CH═NOEt(Z) 3-Br-5-CF₃ CF₂Cl C(O)Et C(O)OCH₃ 3-Br-5-CF₃ CF₂Cl H (D34-1c)CN 3-CH₃-5-CF₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3-CH₃-5-CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-CH₃-5-CF₃ CF₃ H CH₂(D10-2a) 3-CH₃-5-CF₃ CF₃ H CH═NOCH₃(Z) 3-CH₃-5-CF₃ CF₃ H CH═NOEt(Z) 3,5-(CF₃)₂ CHF₂ H CH₂C(O)NHCH₂CF₃ 3,5-(CF₃)₂ CHF₂ H CH(CH₃)C(O)NHCH₂CF₃(D) 3,5-(CF₃)₂ CHF₂ H CH₂(D10-2a) 3,5-(CF₃)₂ CHF₂ H CH═NOCH₃(Z) 3,5-(CF₃)₂ CHF₂ H CH═NOEt(Z) 3,5-(CF₃)₂ CF₃ C(O)OCH₃ CH₃ 3,5-(CF₃)₂ CF₃ C(O)OEt CH₃ 3,5-(CF₃)₂ CF₃ H c-Pr 3,5-(CF₃)₂ CF₃ H CH₂Pr-c 3,5-(CF₃)₂ CF₃ H c-Bu 3,5-(CF₃)₂ CF₃ H CH₂CF₃ 3,5-(CF₃)₂ CF₃ C(O)CH₃ CH₂CF₃ 3,5-(CF₃)₂ CF₃ H CH₂CH₂CF₃ 3,5-(CF₃)₂ CF₃ C(O)OCH₃ CH₂OCH₃ 3,5-(CF₃)₂ CF₃ C(O)OPr-i CH₂OCH₃ 3,5-(CF₃)₂ CF₃ H CH₂OEt 3,5-(CF₃)₂ CF₃ C(O)CH₃ CH₂OEt 3,5-(CF₃)₂ CF₃ C(O)OCH₃ CH₂OEt 3,5-(CF₃)₂ CF₃ C(O)OEt CH₂OEt 3,5-(CF₃)₂ CF₃ C(O)OCH₃ CH₂OPr-i 3,5-(CF₃)₂ CF₃ H CH₂OCH₂CF₃ 3,5-(CF₃)₂ CF₃ C(O)CH₃ CH₂OCH₂CF₃ 3,5-(CF₃)₂ CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3,5-(CF₃)₂ CF₃ C(O)OCH₃ CH₂OC(O)CH₃ 3,5-(CF₃)₂ CF₃ C(O)OCH₃ CH₂OC(O)OCH₃ 3,5-(CF₃)₂ CF₃ H CH(CH₃)OCH₂CF₃ 3,5-(CF₃)₂ CF₃ H E4-1a 3,5-(CF₃)₂ CF₃ C(O)Et E4-1a 3,5-(CF₃)₂ CF₃ C(O)OCH₃ E4-1a 3,5-(CF₃)₂ CF₃ H CH₂CH₂OCH₃ 3,5-(CF₃)₂ CF₃ H CH₂(E4-1a) 3,5-(CF₃)₂ CF₃ H E4-2a(R) 3,5-(CF₃)₂ CF₃ H CH₂CH(OCH₃)₂ 3,5-(CF₃)₂ CF₃ H CH₂(E7-1a) 3,5-(CF₃)₂ CF₃ H CH₂(E7-1b)CH₃ 3,5-(CF₃)₂ CF₃ H CH₂(E4-2a) 3,5-(CF₃)₂ CF₃ H E5-2a 3,5-(CF₃)₂ CF₃ H E5-2b 3,5-(CF₃)₂ CF₃ H E5-2c 3,5-(CF₃)₂ CF₃ H CH₂CH═NOCH₃ 3,5-(CF₃)₂ CF₃ H CH₂C(CH₃)═NOCH₃ 3,5-(CF₃)₂ CF₃ C(O)OPr-i CH₂CN 3,5-(CF₃)₂ CF₃ H CH₂C(O)NHCH₃ 3,5-(CF₃)₂ CF₃ H CH₂C(O)N(CH₃)₂ 3,5-(CF₃)₂ CF₃ H CH₂C(O)NHEt 3,5-(CF₃)₂ CF₃ H CH₂C(O)NHPr-n 3,5-(CF₃)₂ CF₃ H CH₂C(O)NHPr-i 3,5-(CF₃)₂ CF₃ H CH₂C(O)NHCH₂CH₂F 3,5-(CF₃)₂ CF₃ H CH₂C(O)NHCH₂CH₂Cl 3,5-(CF₃)₂ CF₃ H CH₂C(O)NHCH₂CF₃ 3,5-(CF₃)₂ CF₃ H CH₂C(O)NHCH₂CH═CH₂ 3,5-(CF₃)₂ CF₃ H CH₂C(O)NHCH₂C≡CH 3,5-(CF₃)₂ CF₃ H CH(CH₃)C(O)NHCH₂CH₂Cl 3,5-(CF₃)₂ CF₃ H CH(CH₃)C(O)NHCH₂CH₂Cl(D) 3,5-(CF₃)₂ CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3,5-(CF₃)₂ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3,5-(CF₃)₂ CF₃ H T-2 3,5-(CF₃)₂ CF₃ H CH₂CH═CH₂ 3,5-(CF₃)₂ CF₃ H CH₂(Ph-4-NO₂) 3,5-(CF₃)₂ CF₃ H CH₂(Ph-4-CN) 3,5-(CF₃)₂ CF₃ H CH(CH₃)Ph(R) 3,5-(CF₃)₂ CF₃ H CH₂(D8-1a)CH₃ 3,5-(CF₃)₂ CF₃ H CH₂(D8-2b)Cl 3,5-(CF₃)₂ CF₃ H CH₂(D8-2c)Cl 3,5-(CF₃)₂ CF₃ H CH₂(D8-3a)CH₃ 3,5-(CF₃)₂ CF₃ H CH₂(D8-3b)Cl 3,5-(CF₃)₂ CF₃ H CH₂(D10-1a) 3,5-(CF₃)₂ CF₃ H CH₂(D10-2a) 3,5-(CF₃)₂ CF₃ C(O)CH₃ CH₂(D10-2a) 3,5-(CF₃)₂ CF₃ C(O)Et CH₂(D10-2a) 3,5-(CF₃)₂ CF₃ H CH₂(D13-1a) 3,5-(CF₃)₂ CF₃ H CH₂(D16-1a) 3,5-(CF₃)₂ CF₃ H CH₂(D22-1a) 3,5-(CF₃)₂ CF₃ H CH₂(D32-1a) 3,5-(CF₃)₂ CF₃ Et CH₂(D32-1a) 3,5-(CF₃)₂ CF₃ CH₂OCH₃ CH₂(D32-1a) 3,5-(CF₃)₂ CF₃ CH₂CN CH₂(D32-1a) 3,5-(CF₃)₂ CF₃ CH₂C≡CH CH₂(D32-1a) 3,5-(CF₃)₂ CF₃ C(O)CH₃ CH₂(D32-1a) 3,5-(CF₃)₂ CF₃ C(O)Et CH₂(D32-1a) 3,5-(CF₃)₂ CF₃ C(O)Pr-c CH₂(D32-1a) 3,5-(CF₃)₂ CF₃ C(O)Bu-t CH₂(D32-1a) 3,5-(CF₃)₂ CF₃ C(O)CH₂OCH₃ CH₂(D32-1a) 3,5-(CF₃)₂ CF₃ C(O)CH═CH₂ CH₂(D32-1a) 3,5-(CF₃)₂ CF₃ C(O)OCH₃ CH₂(D32-1a) 3,5-(CF₃)₂ CF₃ H CH₂(D32-1a) 3,5-(CF₃)₂ CF₃ H CH(CH₃)(D32-1a) 3,5-(CF₃)₂ CF₃ H T-3 3,5-(CF₃)₂ CF₃ H CH═NOCH₃ 3,5-(CF₃)₂ CF₃ H CH═NOCH₃(Z) 3,5-(CF₃)₂ CF₃ CH₂OCH₃ CH═NOCH₃ 3,5-(CF₃)₂ CF₃ CH₂OEt CH═NOCH₃ 3,5-(CF₃)₂ CF₃ CH₂OC(O)CH₃ CH═NOCH₃ 3,5-(CF₃)₂ CF₃ CH₂CN CH═NOCH₃ 3,5-(CF₃)₂ CF₃ H CH═NOEt 3,5-(CF₃)₂ CF₃ H CH═NOEt(Z) 3,5-(CF₃)₂ CF₃ C(O)Et C(O)OCH₃ 3,5-(CF₃)₂ CF₃ H C(O)OEt 3,5-(CF₃)₂ CF₃ H C(O)OPr-i 3,5-(CF₃)₂ CF₃ C(O)CH₃ C(O)OPr-i 3,5-(CF₃)₂ CF₃ C(O)Et C(O)OPr-i 3,5-(CF₃)₂ CF₃ C(O)Bu-t C(O)OPr-i 3,5-(CF₃)₂ CF₃ C(O)CH₂OCH₃ C(O)OPr-i 3,5-(CF₃)₂ CF₃ C(O)OCH₃ C(O)OPr-i 3,5-(CF₃)₂ CF₃ C(O)OEt C(O)OPr-i 3,5-(CF₃)₂ CF₃ H C(O)NH₂ 3,5-(CF₃)₂ CF₃ CH₃ C(O)NH₂ 3,5-(CF₃)₂ CF₃ H C(O)NHEt 3,5-(CF₃)₂ CF₃ H C(O)NHCH₂CF₃ 3,5-(CF₃)₂ CF₃ —C(NH₂)(OCH₃)— 3,5-(CF₃)₂ CF₃ —C(NH₂)(OEt)— 3,5-(CF₃)₂ CF₃ —C(NHCH₃)(OCH₃)— 3,5-(CF₃)₂ CF₃ H C(S)OPr-i 3,5-(CF₃)₂ CF₃ CH₂OC(O)CH₃ (D34-1c)Cl 3,5-(CF₃)₂ CF₃ C(O)CH₃ (D34-1c)Cl 3,5-(CF₃)₂ CF₃ C(O)Pr-c (D34-1c)Cl 3,5-(CF₃)₂ CF₃ C(O)OCH₃ (D34-1c)Cl 3,5-(CF₃)₂ CF₃ H (D34-1c)CN 3,5-(CF₃)₂ CF₃ CH₃ (D34-1c)CN 3,5-(CF₃)₂ CF₃ CH₂OCH₃ (D34-1c)CN 3,5-(CF₃)₂ CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3,5-(CF₃)₂ CF₃ C(O)Pr-i (D34-1c)CN 3,5-(CF₃)₂ CF₃ C(O)OCH₃ (D34-1c)CN 3,5-(CF₃)₂ CF₃ CH₂OCH₃ D34-3a 3,5-(CF₃)₂ CF₃ CH₂CN D34-3a 3,5-(CF₃)₂ CF₃ C(O)Et D34-3a 3,5-(CF₃)₂ CF₃ C(O)Pr-i D34-3a 3,5-(CF₃)₂ CF₃ CH₃ D35-1a 3,5-(CF₃)₂ CF₃ C(O)OCH₃ (D35-1c)Cl 3,5-(CF₃)₂ CF₃ H N(CH₃)Ph 3,5-(CF₃)₂ CF₃ H N(CH₂CH═CH₂)Ph 3,5-(CF₃)₂ CF₃ H N(CH₂C≡CH)Ph 3,5-(CF₃)₂ CF₃ H N(CH₃)(D32-1a) 3,5-(CF₃)₂ CF₃ H NH(D34-1a) 3,5-(CF₃)₂ CF₃ CH₃ NH(D34-1a) 3,5-(CF₃)₂ CF₃ H N(CH₃)(D34-1a) 3,5-(CF₃)₂ CF₃ H N(Et)(D34-1a) 3,5-(CF₃)₂ CF₂Cl C(O)OCH₃ CH₂OEt 3,5-(CF₃)₂ CF₂Cl H CH₂OCH₂CF₃ 3,5-(CF₃)₂ CF₂Cl C(O)OCH₃ CH₂OCH₂CF₃ 3,5-(CF₃)₂ CF₂Cl H E4-1a 3,5-(CF₃)₂ CF₂Cl H CH₂C(O)NHCH₂CF₃ 3,5-(CF₃)₂ CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃ 3,5-(CF₃)₂ CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3,5-(CF₃)₂ CF₂Cl H CH₂(D10-2a) 3,5-(CF₃)₂ CF₂Cl H CH₂(D32-1a) 3,5-(CF₃)₂ CF₂Cl C(O)CH₃ CH₂(D32-1a) 3,5-(CF₃)₂ CF₂Cl C(O)OCH₃ CH₂(D32-1a) 3,5-(CF₃)₂ CF₂Cl H CH═NOCH₃(Z) 3,5-(CF₃)₂ CF₂Cl H CH═NOEt(Z) 3,5-(CF₃)₂ CF₂Cl C(O)Et C(O)OCH₃ 3,5-(CF₃)₂ CF₂Cl C(O)CH₃ (D34-1c)Cl 3,5-(CF₃)₂ CF₂Cl C(O)OCH₃ (D34-1c)Cl 3,5-(CF₃)₂ CF₂Cl H (D34-1c)CN 3,5-(CF₃)₂ CF₂Cl CH₃ (D34-1c)CN 3,5-(CF₃)₂ CF₂Cl CH₂OC(O)CH₃ (D34-1c)CN 3,5-(CF₃)₂ CF₂Cl C(O)Pr-i (D34-1c)CN 3,5-(CF₃)₂ CF₂Br H CH₂C(O)NHCH₂CF₃ 3,5-(CF₃)₂ CF₂Br H CH(CH₃)C(O)NHCH₂CF₃(D) 3,5-(CF₃)₂ CF₂Br H CH₂(D10-2a) 3,5-(CF₃)₂ CF₂Br H CH═NOCH₃(Z) 3,5-(CF₃)₂ CF₂Br H CH═NOEt(Z) 3,5-(CF₃)₂ CF₂CHF₂ H CH₂C(O)NHCH₂CF₃ 3,5-(CF₃)₂ CF₂CHF₂ H CH(CH₃)C(O)NHCH₂CF₃(D) 3,5-(CF₃)₂ CF₂CHF₂ H CH₂(D10-2a) 3,5-(CF₃)₂ CF₂CHF₂ H CH═NOCH₃(Z) 3,5-(CF₃)₂ CF₂CHF₂ H CH═NOEt(Z) 3-CF₃-5-OCH₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3-CF₃-5-OCH₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-CF₃-5-OCH₃ CF₃ H CH₂(D10-2a) 3-CF₃-5-OCH₃ CF₃ H CH═NOCH₃(Z) 3-CF₃-5-OCH₃ CF₃ H CH═NOEt(Z) 3-Cl-5-OCHF₂ CF₃ C(O)OCH₃ CH₂OEt 3-Cl-5-OCHF₂ CF₃ H CH₂OCH₂CF₃ 3-Cl-5-OCHF₂ CF₃ C(O)OCH₃ CH₂OCH₂CF 3-Cl-5-OCHF₂ CF₃ H E4-1a 3-Cl-5-OCHF₂ CF₃ H CH₂C(O)NHCH₂CF₃ 3-Cl-5-OCHF₂ CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3-Cl-5-OCHF₂ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Cl-5-OCHF₂ CF₃ H CH₂(D10-2a) 3-Cl-5-OCHF₂ CF₃ H CH₂(D32-1a) 3-Cl-5-OCHF₂ CF₃ C(O)CH₃ CH₂(D32-1a) 3-Cl-5-OCHF₂ CF₃ C(O)OCH₃ CH₂(D32-1a) 3-Cl-5-OCHF₂ CF₃ H CH═NOCH₃(Z) 3-Cl-5-OCHF₂ CF₃ H CH═NOEt(Z) 3-Cl-5-OCHF₂ CF₃ C(O)Et C(O)OCH₃ 3-Cl-5-OCHF₂ CF₃ C(O)CH₃ (D34-1c)Cl 3-Cl-5-OCHF₂ CF₃ C(O)OCH₃ (D34-1c)Cl 3-Cl-5-OCHF₂ CF₃ H (D34-1c)CN 3-Cl-5-OCHF₂ CF₃ CH₃ (D34-1c)CN 3-Cl-5-OCHF₂ CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3-Cl-5-OCHF₂ CF₃ C(O)Pr-i (D34-1c)CN 3-Cl-5-OCHF₂ CF₂Cl H CH₂C(O)NHCH₂CF₃ 3-Cl-5-OCHF₂ CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Cl-5-OCHF₂ CF₂Cl H CH₂(D10-2a) 3-Cl-5-OCHF₂ CF₂Cl H CH═NOCH₃(Z) 3-Cl-5-OCHF₂ CF₂Cl H CH═NOEt(Z) 3-Br-5-OCHF₂ CF₃ C(O)OCH₃ CH₂OEt 3-Br-5-OCHF₂ CF₃ H CH₂OCH₂CF₃ 3-Br-5-OCHF₂ CF₃ H E4-1a 3-Br-5-OCHF₂ CF₃ H CH₂C(O)NHCH₂CF₃ 3-Br-5-OCHF₂ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Br-5-OCHF₂ CF₃ H CH₂(D10-2a) 3-Br-5-OCHF₂ CF₃ H CH═NOCH₃(Z) 3-Br-5-OCHF₂ CF₃ H CH═NOEt(Z) 3-Br-5-OCHF₂ CF₃ C(O)Et C(O)OCH₃ 3-Br-5-OCHF₂ CF₃ H (D34-1c)CN 3-CF₃-5-OCHF₂ CF₃ C(O)OCH₃ CH₂OEt 3-CF₃-5-OCHF₂ CF₃ H CH₂OCH₂CF₃ 3-CF₃-5-OCHF₂ CF₃ H E4-1a 3-CF₃-5-OCHF₂ CF₃ H CH₂C(O)NHCH₂CF₃ 3-CF₃-5-OCHF₂ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-CF₃-5-OCHF₂ CF₃ H CH₂(D10-2a) 3-CF₃-5-OCHF₂ CF₃ H CH═NOCH₃(Z) 3-CF₃-5-OCHF₂ CF₃ H CH═NOEt(Z) 3-CF₃-5-OCHF₂ CF₃ C(O)Et C(O)OCH₃ 3-CF₃-5-OCHF₂ CF₃ H (D34-1c)CN 3-Cl-5-OCF₃ CF₃ C(O)OCH₃ CH₂OEt 3-Cl-5-OCF₃ CF₃ H CH₂OCH₂CF₃ 3-Cl-5-OCF₃ CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3-Cl-5-OCF₃ CF₃ H E4-1a 3-Cl-5-OCF₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3-Cl-5-OCF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3-Cl-5-OCF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Cl-5-OCF₃ CF₃ H CH₂(D10-2a) 3-Cl-5-OCF₃ CF₃ H CH₂(D32-1a) 3-Cl-5-OCF₃ CF₃ C(O)CH₃ CH₂(D32-1a) 3-Cl-5-OCF₃ CF₃ C(O)OCH₃ CH₂(D32-1a) 3-Cl-5-OCF₃ CF₃ H CH═NOCH₃(Z) 3-Cl-5-OCF₃ CF₃ H CH═NOEt(Z) 3-Cl-5-OCF₃ CF₃ C(O)Et C(O)OCH₃ 3-Cl-5-OCF₃ CF₃ C(O)CH₃ (D34-1c)Cl 3-Cl-5-OCF₃ CF₃ C(O)OCH₃ (D34-1c)Cl 3-Cl-5-OCF₃ CF₃ H (D34-1c)CN 3-Cl-5-OCF₃ CF₃ CH₃ (D34-1c)CN 3-Cl-5-OCF₃ CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3-Cl-5-OCF₃ CF₃ C(O)Pr-i (D34-1c)CN 3-Cl-5-OCF₃ CF₂Cl H CH₂C(O)NHCH₂CF₃ 3-Cl-5-OCF₃ CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Cl-5-OCF₃ CF₂Cl H CH₂(D10-2a) 3-Cl-5-OCF₃ CF₂Cl H CH═NOCH₃(Z) 3-Cl-5-OCF₃ CF₂Cl H CH═NOEt(Z) 3-Br-5-OCF₃ CF₃ C(O)OCH₃ CH₂OEt 3-Br-5-OCF₃ CF₃ H CH₂OCH₂CF₃ 3-Br-5-OCF₃ CF₃ H E4-1a 3-Br-5-OCF₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3-Br-5-OCF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Br-5-OCF₃ CF₃ H CH₂(D10-2a) 3-Br-5-OCF₃ CF₃ H CH═NOCH₃(Z) 3-Br-5-OCF₃ CF₃ H CH═NOEt(Z) 3-Br-5-OCF₃ CF₃ C(O)Et C(O)OCH₃ 3-Br-5-OCF₃ CF₃ H (D34-1c)CN 3-CF₃-5-OCF₃ CF₃ C(O)OCH₃ CH₂OEt 3-CF₃-5-OCF₃ CF₃ H CH₂OCH₂CF₃ 3-CF₃-5-OCF₃ CF₃ H E4-1a 3-CF₃-5-OCF₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3-CF₃-5-OCF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-CF₃-5-OCF₃ CF₃ H CH₂(D10-2a) 3-CF₃-5-OCF₃ CF₃ H CH═NOCH₃(Z) 3-CF₃-5-OCF₃ CF₃ H CH═NOEt(Z) 3-CF₃-5-OCF₃ CF₃ C(O)Et C(O)OCH₃ 3-CF₃-5-OCF₃ CF₃ H (D34-1c)CN 3-Cl-5-SCF₃ CF₃ C(O)OCH₃ CH₂OEt 3-Cl-5-SCF₃ CF₃ H CH₂OCH₂CF₃ 3-Cl-5-SCF₃ CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3-Cl-5-SCF₃ CF₃ H E4-1a 3-Cl-5-SCF₃ CF₃ H CH₂C(O)NHCH₂F₃ 3-Cl-5-SCF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3-Cl-5-SCF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Cl-5-SCF₃ CF₃ H CH₂(D10-2a) 3-Cl-5-SCF₃ CF₃ H CH₂(D32-1a) 3-Cl-5-SCF₃ CF₃ C(O)CH₃ CH₂(D32-1a) 3-Cl-5-SCF₃ CF₃ C(O)OCH₃ CH₂(D32-1a) 3-Cl-5-SCF₃ CF₃ H CH═NOCH₃(Z) 3-Cl-5-SCF₃ CF₃ H CH═NOEt(Z) 3-Cl-5-SCF₃ CF₃ C(O)Et C(O)OCH₃ 3-Cl-5-SCF₃ CF₃ C(O)CH₃ (D34-1c)Cl 3-Cl-5-SCF₃ CF₃ C(O)OCH₃ (D34-1c)Cl 3-Cl-5-SCF₃ CF₃ H (D34-1c)CN 3-Cl-5-SCF₃ CF₃ CH₃ (D34-1c)CN 3-Cl-5-SCF₃ CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3-Cl-5-SCF₃ CF₃ C(O)Pr-i (D34-1c)CN 3-Cl-5-SCF₃ CF₂Cl H CH₂C(O)NHCH₂CF₃ 3-Cl-5-SCF₃ CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Cl-5-SCF₃ CF₂Cl H CH₂(D10-2a) 3-Cl-5-SCF₃ CF₂Cl H CH═NOCH₃(Z) 3-Cl-5-SCF₃ CF₂Cl H CH═NOEt(Z) 3-Br-5-SCF₃ CF₃ C(O)OCH₃ CH₂OEt 3-Br-5-SCF₃ CF₃ H CH₂OCH₂CF₃ 3-Br-5-SCF₃ CF₃ H E4-1a 3-Br-5-SCF₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3-Br-5-SCF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Br-5-SCF₃ CF₃ H CH₂(D10-2a) 3-Br-5-SCF₃ CF₃ H CH═NOCH₃(Z) 3-Br-5-SCF₃ CF₃ H CH═NOEt(Z) 3-Br-5-SCF₃ CF₃ C(O)Et C(O)OCH₃ 3-Br-5-SCF₃ CF₃ H (D34-1c)CN 3-CF₃-5-NO₂ CF₃ H CH₂C(O)NHCH₂CF₃ 3-CF₃-5-NO₂ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-CF₃-5-NO₂ CF₃ H CH₂(D10-2a) 3-CF₃-5-NO₂ CF₃ H CH═NOCH₃(Z) 3-CF₃-5-NO₂ CF₃ H CH═NOEt(Z) 3-Cl-5-CN CF₃ H CH₂C(O)NHCH₂CF₃ 3-Cl-5-CN CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Cl-5-CN CF₃ H CH₂(D10-2a) 3-Cl-5-CN CF₃ H CH═NOCH₃(Z) 3-Cl-5-CN CF₃ H CH═NOEt(Z) 3-Br-5-CN CF₃ H CH₂C(O)NHCH₂CF₃ 3-Br-5-CN CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Br-5-CN CF₃ H CH₂(D10-2a) 3-Br-5-CN CF₃ H CH═NOCH₃(Z) 3-Br-5-CN CF₃ H CH═NOEt(Z) 3-CF₃-5-CN CF₃ C(O)OCH₃ CH₂OEt 3-CF₃-5-CN CF₃ H CH₂OCH₂CF₃ 3-CF₃-5-CN CF₃ H E4-1a 3-CF₃-5-CN CF₃ H CH₂C(O)NHCH₂CF₃ 3-CF₃-5-CN CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-CF₃-5-CN CF₃ H CH₂(D10-2a) 3-CF₃-5-CN CF₃ H CH═NOCH₃(Z) 3-CF₃-5-CN CF₃ H CH═NOEt(Z) 3-CF₃-5-CN CF₃ C(O)Et C(O)OCH₃ 3-CF₃-5-CN CF₃ H (D34-1c)CN 3,4,5-F₃ CF₃ C(O)OCH₃ CH₂OEt 3,4,5-F₃ CF₃ H CH₂OCH₂CF₃ 3,4,5-F₃ CF₃ H E4-1a 3,4,5-F₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3,4,5-F₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3,4,5-F₃ CF₃ H CH₂(D10-2a) 3,4,5-F₃ CF₃ H CH═NOCH₃(Z) 3,4,5-F₃ CF₃ H CH═NOEt(Z) 3,4,5-F₃ CF₃ C(O)Et C(O)OCH₃ 3,4,5-F₃ CF₃ H (D34-1c)CN 3,5-Cl₂-4-F CF₃ C(O)CH₃ CH₂CF₃ 3,5-Cl₂-4-F CF₃ C(O)OCH₃ CH₂OCH₃ 3,5-Cl₂-4-F CF₃ C(O)OCH₃ CH₂OEt 3,5-Cl₂-4-F CF₃ C(O)OCH₃ CH₂OPr-i 3,5-Cl₂-4-F CF₃ H CH₂OCH₂CF₃ 3,5-Cl₂-4-F CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3,5-Cl₂-4-F CF₃ H E4-1a 3,5-Cl₂-4-F CF₃ H CH₂C(O)NHCH₂CH₂Cl 3,5-Cl₂-4-F CF₃ H CH₂C(O)NHCH₂CF₃ 3,5-Cl₂-4-F CF₃ H CH(CH₃)C(O)NHCH₂CH₂Cl 3,5-Cl₂-4-F CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3,5-Cl₂-4-F CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3,5-Cl₂-4-F CF₃ H CH₂(D10-2a) 3,5-Cl₂-4-F CF₃ C(O)CH₃ CH₂(D10-2a) 3,5-Cl₂-4-F CF₃ C(O)Et CH₂(D10-2a) 3,5-Cl₂-4-F CF₃ H CH₂(D32-1a) 3,5-Cl₂-4-F CF₃ C(O)CH₃ CH₂(D32-1a) 3,5-Cl₂-4-F CF₃ C(O)Et CH₂(D32-1a) 3,5-Cl₂-4-F CF₃ C(O)OCH₃ CH₂(D32-1a) 3,5-Cl₂-4-F CF₃ H CH═NOCH₃(Z) 3,5-Cl₂-4-F CF₃ CH₂OCH₃ CH═NOCH₃ 3,5-Cl₂-4-F CF₃ CH₂OC(O)CH₃ CH═NOCH₃ 3,5-Cl₂-4-F CF₃ H CH═NOEt(Z) 3,5-Cl₂-4-F CF₃ C(O)Et C(O)OCH₃ 3,5-Cl₂-4-F CF₃ CH₂OC(O)CH₃ (D34-1c)Cl 3,5-Cl₂-4-F CF₃ C(O)CH₃ (D34-1c)Cl 3,5-Cl₂-4-F CF₃ C(O)Pr-c (D34-1c)Cl 3,5-Cl₂-4-F CF₃ C(O)OCH₃ (D34-1c)Cl 3,5-Cl₂-4-F CF₃ H (D34-1c)CN 3,5-Cl₂-4-F CF₃ CH₃ (D34-1c)CN 3,5-Cl₂-4-F CF₃ CH₂OCH₃ (D34-1c)CN 3,5-Cl₂-4-F CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3,5-Cl₂-4-F CF₃ C(O)Pr-i (D34-1c)CN 3,5-Cl₂-4-F CF₃ C(O)OCH₃ (D34-1c)CN 3,5-Cl₂-4-F CF₃ CH₂OCH₃ D34-3a 3,5-Cl₂-4-F CF₃ C(O)Et D34-3a 3,5-Cl₂-4-F CF₃ C(O)Pr-i D34-3a 3,5-Cl₂-4-F CF₃ C(O)OCH₃ (D35-1c)Cl 3,5-Cl₂-4-F CF₃ H N(CH₃)Ph 3,5-Cl₂-4-F CF₃ H N(CH₃)(D34-1a) 3,5-Cl₂-4-F CF₂Cl C(O)OCH₃ CH₂OEt 3,5-Cl₂-4-F CF₂Cl H CH₂OCH₂CF₃ 3,5-Cl₂-4-F CF₂Cl H E4-1a 3,5-Cl₂-4-F CF₂Cl H CH₂C(O)NHCH₂CF₃ 3,5-Cl₂-4-F CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3,5-Cl₂-4-F CF₂Cl H CH₂(D10-2a) 3,5-Cl₂-4-F CF₂Cl H CH═NOCH₃(Z) 3,5-Cl₂-4-F CF₂Cl H CH═NOEt(Z) 3,5-Cl₂-4-F CF₂Cl C(O)Et C(O)OCH₃ 3,5-Cl₂-4-F CF₂Cl H (D34-1c)CN 3,4,5-Cl₃ CF₃ C(O)CH₃ CH₂CF₃ 3,4,5-Cl₃ CF₃ C(O)OCH₃ CH₂OCH₃ 3,4,5-Cl₃ CF₃ C(O)OCH₃ CH₂OEt 3,4,5-Cl₃ CF₃ C(O)OCH₃ CH₂OPr-i 3,4,5-Cl₃ CF₃ H CH₂OCH₂CF₃ 3,4,5-Cl₃ CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3,4,5-Cl₃ CF₃ H E4-1a 3,4,5-Cl₃ CF₃ H CH₂C(O)NHCH₂CH₂Cl 3,4,5-Cl₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3,4,5-Cl₃ CF₃ H CH(CH₃)C(O)NHCH₂CH₂Cl 3,4,5-Cl₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3,4,5-Cl₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3,4,5-Cl₃ CF₃ H CH₂(D10-2a) 3,4,5-Cl₃ CF₃ C(O)CH₃ CH₂(D10-2a) 3,4,5-Cl₃ CF₃ C(O)Et CH₂(D10-2a) 3,4,5-Cl₃ CF₃ H CH₂(D32-1a) 3,4,5-Cl₃ CF₃ C(O)CH₃ CH₂(D32-1a) 3,4,5-Cl₃ CF₃ C(O)Et CH₂(D32-1a) 3,4,5-Cl₃ CF₃ C(O)OCH₃ CH₂(D32-1a) 3,4,5-Cl₃ CF₃ H CH═NOCH₃(Z) 3,4,5-Cl₃ CF₃ CH₂OCH₃ CH═NOCH₃ 3,4,5-Cl₃ CF₃ CH₂OC(O)CH₃ CH═NOCH₃ 3,4,5-Cl₃ CF₃ H CH═NOEt(Z) 3,4,5-Cl₃ CF₃ C(O)Et C(O)OCH₃ 3,4,5-Cl₃ CF₃ CH₂OC(O)CH₃ (D34-1c)Cl 3,4,5-Cl₃ CF₃ C(O)CH₃ (D34-1c)Cl 3,4,5-Cl₃ CF₃ C(O)Pr-c (D34-1c)Cl 3,4,5-Cl₃ CF₃ C(O)OCH₃ (D34-1c)Cl 3,4,5-Cl₃ CF₃ H (D34-1c)CN 3,4,5-Cl₃ CF₃ CH₃ (D34-1c)CN 3,4,5-Cl₃ CF₃ CH₂OCH₃ (D34-1c)CN 3,4,5-Cl₃ CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3,4,5-Cl₃ CF₃ C(O)Pr-i (D34-1c)CN 3,4,5-Cl₃ CF₃ C(O)OCH₃ (D34-1c)CN 3,4,5-Cl₃ CF₃ CH₂OCH₃ D34-3a 3,4,5-Cl₃ CF₃ C(O)Et D34-3a 3,4,5-Cl₃ CF₃ C(O)Pr-i D34-3a 3,4,5-Cl₃ CF₃ C(O)OCH₃ (D35-1c)Cl 3,4,5-Cl₃ CF₃ H N(CH₃)Ph 3,4,5-Cl₃ CF₃ H N(CH₃)(D34-1a) 3,4,5-Cl₃ CF₂Cl C(O)OCH₃ CH₂OEt 3,4,5-Cl₃ CF₂Cl H CH₂OCH₂CF₃ 3,4,5-Cl₃ CF₂Cl H E4-1a 3,4,5-Cl₃ CF₂Cl H CH₂C(O)NHCH₂CF₃ 3,4,5-Cl₃ CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3,4,5-Cl₃ CF₂Cl H CH₂(D10-2a) 3,4,5-Cl₃ CF₂Cl H CH═NOCH₃(Z) 3,4,5-Cl₃ CF₂Cl H CH═NOEt(Z) 3,4,5-Cl₃ CF₂Cl C(O)Et C(O)OCH₃ 3,4,5-Cl₃ CF₂Cl H (D34-1c)CN 3,5-Br₂-4-F CF₃ C(O)CH₃ CH₂CF₃ 3,5-Br₂-4-F CF₃ C(O)OCH₃ CH₂OCH₃ 3,5-Br₂-4-F CF₃ C(O)OCH₃ CH₂OEt 3,5-Br₂-4-F CF₃ C(O)OCH₃ CH₂OPr-i 3,5-Br₂-4-F CF₃ H CH₂OCH₂CF₃ 3,5-Br₂-4-F CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3,5-Br₂-4-F CF₃ H E4-1a 3,5-Br₂-4-F CF₃ H CH₂C(O)NHCH₂CH₂Cl 3,5-Br₂-4-F CF₃ H CH₂C(O)NHCH₂CF₃ 3,5-Br₂-4-F CF₃ H CH(CH₃)C(O)NHCH₂CH₂Cl 3,5-Br₂-4-F CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3,5-Br₂-4-F CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3,5-Br₂-4-F CF₃ H CH₂(D10-2a) 3,5-Br₂-4-F CF₃ C(O)CH₃ CH₂(D10-2a) 3,5-Br₂-4-F CF₃ C(O)Et CH₂(D10-2a) 3,5-Br₂-4-F CF₃ H CH₂(D32-1a) 3,5-Br₂-4-F CF₃ C(O)CH₃ CH₂(D32-1a) 3,5-Br₂-4-F CF₃ C(O)Et CH₂(D32-1a) 3,5-Br₂-4-F CF₃ C(O)OCH₃ CH₂(D32-1a) 3,5-Br₂-4-F CF₃ H CH═NOCH₃(Z) 3,5-Br₂-4-F CF₃ CH₂OCH₃ CH═NOCH₃ 3,5-Br₂-4-F CF₃ CH₂OC(O)CH₃ CH═NOCH₃ 3,5-Br₂-4-F CF₃ H CH═NOEt(Z) 3,5-Br₂-4-F CF₃ C(O)Et C(O)OCH₃ 3,5-Br₂-4-F CF₃ CH₂OC(O)CH₃ (D34-1c)Cl 3,5-Br₂-4-F CF₃ C(O)CH₃ (D34-1c)Cl 3,5-Br₂-4-F CF₃ C(O)Pr-c (D34-1c)Cl 3,5-Br₂-4-F CF₃ C(O)OCH₃ (D34-1c)Cl 3,5-Br₂-4-F CF₃ H (D34-1c)CN 3,5-Br₂-4-F CF₃ CH₃ (D34-1c)CN 3,5-Br₂-4-F CF₃ CH₂OCH₃ (D34-1c)CN 3,5-Br₂-4-F CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3,5-Br₂-4-F CF₃ C(O)Pr-i (D34-1c)CN 3,5-Br₂-4-F CF₃ C(O)OCH₃ (D34-1c)CN 3,5-Br₂-4-F CF₃ CH₂OCH₃ D34-3a 3,5-Br₂-4-F CF₃ C(O)Et D34-3a 3,5-Br₂-4-F CF₃ C(O)Pr-i D34-3a 3,5-Br₂-4-F CF₃ C(O)OCH₃ (D35-1c)Cl 3,5-Br₂-4-F CF₃ H N(CH₃)Ph 3,5-Br₂-4-F CF₂Cl H N(CH₃)(D34-1a) 3,5-Br₂-4-F CF₂Cl C(O)OCH₃ CH₂OEt 3,5-Br₂-4-F CF₂Cl H CH₂OCH₂CF₃ 3,5-Br₂-4-F CF₂Cl H E4-1a 3,5-Br₂-4-F CF₂Cl H CH₂C(O)NHCH₂CF₃ 3,5-Br₂-4-F CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3,5-Br₂-4-F CF₂Cl H CH₂(D10-2a) 3,5-Br₂-4-F CF₂Cl H CH═NOCH₃(Z) 3,5-Br₂-4-F CF₂Cl H CH═NOEt(Z) 3,5-Br₂-4-F CF₂Cl C(O)Et C(O)OCH₃ 3,4,5-Br₃ CF₃ H (D34-1c)CN 3,4,5-Br₃ CF₃ C(O)OCH₃ CH₂OEt 3,4,5-Br₃ CF₃ H CH₂OCH₂CF₃ 3,4,5-Br₃ CF₃ H E4-1a 3,4,5-Br₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3,4,5-Br₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3,4,5-Br₃ CF₃ H CH₂(D10-2a) 3,4,5-Br₃ CF₃ H CH═NOCH₃(Z) 3,4,5-Br₃ CF₃ H CH═NOEt(Z) 3,4,5-Br₃ CF₃ C(O)Et C(O)OCH₃ 3,4,5-Br₃ CF₃ H (D34-1c)CN 3,4-Cl₂-5-CH₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3,4-Cl₂-5-CH₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3,4-Cl₂-5-CH₃ CF₃ H CH₂(D10-2a) 3,4-Cl₂-5-CH₃ CF₃ H CH═NOCH₃(Z) 3,4-Cl₂-5-CH₃ CF₃ H CH═NOEt(Z) 3,4-F₂-5-CF₃ CF₃ C(O)CH₃ CH₂CF₃ 3,4-F₂-5-CF₃ CF₃ C(O)OCH₃ CH₂OCH₃ 3,4-F₂-5-CF₃ CF₃ C(O)OCH₃ CH₂OEt 3,4-F₂-5-CF₃ CF₃ H CH₂OCH₂CF₃ 3,4-F₂-5-CF₃ CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3,4-F₂-5-CF₃ CF₃ H E4-1a 3,4-F₂-5-CF₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3,4-F₂-5-CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CH₂Cl 3,4-F₂-5-CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3,4-F₂-5-CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3,4-F₂-5-CF₃ CF₃ H CH₂(D10-2a) 3,4-F₂-5-CF₃ CF₃ H CH₂(D32-1a) 3,4-F₂-5-CF₃ CF₃ C(O)CH₃ CH₂(D32-1a) 3,4-F₂-5-CF₃ CF₃ C(O)Et CH₂(D32-1a) 3,4-F₂-5-CF₃ CF₃ C(O)OCH₃ CH₂(D32-1a) 3,4-F₂-5-CF₃ CF₃ H CH═NOCH₃(Z) 3,4-F₂-5-CF₃ CF₃ CH₂OCH₃ CH═NOCH₃ 3,4-F₂-5-CF₃ CF₃ H CH═NOEt(Z) 3,4-F₂-5-CF₃ CF₃ C(O)Et C(O)OCH₃ 3,4-F₂-5-CF₃ CF₃ CH₂OC(O)CH₃ (D34-1c)Cl 3,4-F₂-5-CF₃ CF₃ C(O)CH₃ (D34-1c)Cl 3,4-F₂-5-CF₃ CF₃ C(O)Pr-c (D34-1c)Cl 3,4-F₂-5-CF₃ CF₃ CH(O)OCH₃ (D34-1c)Cl 3,4-F₂-5-CF₃ CF₃ H (D34-1c)CN 3,4-F₂-5-CF₃ CF₃ CH₃ (D34-1c)CN 3,4-F₂-5-CF₃ CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3,4-F₂-5-CF₃ CF₃ C(O)Pr-i (D34-1c)CN 3,4-F₂-5-CF₃ CF₃ CH(O)OCH₃ (D34-1c)CN 3,4-F₂-5-CF₃ CF₃ C(O)Et D34-3a 3,4-F₂-5-CF₃ CF₃ C(O)Pr-i D34-3a 3,4-F₂-5-CF₃ CF₂Cl CH(O)OCH₃ CH₂OEt 3,4-F₂-5-CF₃ CF₂Cl H CH₂OCH₂CF₃ 3,4-F₂-5-CF₃ CF₂Cl H E4-1a 3,4-F₂-5-CF₃ CF₂Cl H CH₂C(O)NHCH₂CF₃ 3,4-F₂-5-CF₃ CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3,4-F₂-5-CF₃ CF₂Cl H CH₂(D10-2a) 3,4-F₂-5-CF₃ CF₂Cl H CH═NOCH₃(Z) 3,4-F₂-5-CF₃ CF₂Cl H CH═NOEt(Z) 3,4-F₂-5-CF₃ CF₂Cl C(O)Et C(O)OCH₃ 3,4-F₂-5-CF₃ CF₂Cl H (D34-1c)CN 3-Cl-4-F-5-CF₃ CF₃ C(O)CH₃ CH₂CF₃ 3-Cl-4-F-5-CF₃ CF₃ C(O)OCH₃ CH₂OCH₃ 3-Cl-4-F-5-CF₃ CF₃ C(O)OCH₃ CH₂OEt 3-Cl-4-F-5-CF₃ CF₃ H CH₂OCH₂CF₃ 3-Cl-4-F-5-CF₃ CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3-Cl-4-F-5-CF₃ CF₃ H E4-1a 3-Cl-4-F-5-CF₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3-Cl-4-F-5-CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CH₂Cl 3-Cl-4-F-5-CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3-Cl-4-F-5-CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Cl-4-F-5-CF₃ CF₃ H CH₂(D10-2a) 3-Cl-4-F-5-CF₃ CF₃ H CH₂(D32-1a) 3-Cl-4-F-5-CF₃ CF₃ C(O)CH₃ CH₂(D32-1a) 3-Cl-4-F-5-CF₃ CF₃ C(O)Et CH₂(D32-1a) 3-Cl-4-F-5-CF₃ CF₃ C(O)OCH₃ CH₂(D32-1a) 3-Cl-4-F-5-CF₃ CF₃ H CH═NOCH₃(Z) 3-Cl-4-F-5-CF₃ CF₃ CH₂OCH₃ CH═NOCH₃ 3-Cl-4-F-5-CF₃ CF₃ H CH═NOEt(Z) 3-Cl-4-F-5-CF₃ CF₃ C(O)Et C(O)OCH₃ 3-Cl-4-F-5-CF₃ CF₃ CH₂OC(O)CH₃ (D34-1c)Cl 3-Cl-4-F-5-CF₃ CF₃ C(O)CH₃ (D34-1c)Cl 3-Cl-4-F-5-CF₃ CF₃ C(O)Pr-c (D34-1c)Cl 3-Cl-4-F-5-CF₃ CF₃ C(O)OCH₃ (D34-1c)Cl 3-Cl-4-F-5-CF₃ CF₃ H (D34-1c)CN 3-Cl-4-F-5-CF₃ CF₃ CH₃ (D34-1c)CN 3-Cl-4-F-5-CF₃ CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3-Cl-4-F-5-CF₃ CF₃ C(O)Pr-i (D34-1c)CN 3-Cl-4-F-5-CF₃ CF₃ C(O)OCH₃ (D34-1c)CN 3-Cl-4-F-5-CF₃ CF₃ C(O)Et D34-3a 3-Cl-4-F-5-CF₃ CF₃ C(O)Pr-i D34-3a 3-Cl-4-F-5-CF₃ CF₂Cl C(O)OCH₃ CH₂OEt 3-Cl-4-F-5-CF₃ CF₂Cl H CH₂OCH₂CF₃ 3-Cl-4-F-5-CF₃ CF₂Cl H E4-1a 3-Cl-4-F-5-CF₃ CF₂Cl H CH₂C(O)NHCH₂CF₃ 3-Cl-4-F-5-CF₃ CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3-Cl-4-F-5-CF₃ CF₂Cl H CH₂(D10-2a) 3-Cl-4-F-5-CF₃ CF₂Cl H CH═NOCH₃(Z) 3-Cl-4-F-5-CF₃ CF₂Cl H CH═NOEt(Z) 3-Cl-4-F-5-CF₃ CF₂Cl C(O)Et C(O)OCH₃ 3-Cl-4-F-5-CF₃ CF₂Cl H (D34-1c)CN 3,4-Cl₂-5-CF₃ CF₃ C(O)CH₃ CH₂CF₃ 3,4-Cl₂-5-CF₃ CF₃ C(O)OCH₃ CH₂OCH₃ 3,4-Cl₂-5-CF₃ CF₃ C(O)OCH₃ CH₂OEt 3,4-Cl₂-5-CF₃ CF₃ H CH₂OCH₂CF₃ 3,4-Cl₂-5-CF₃ CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3,4-Cl₂-5-CF₃ CF₃ H E4-1a 3,4-Cl₂-5-CF₃ CF₃ H CH₂C(O)NHCH₂CF₃ 3,4-Cl₂-5-CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CH₂Cl 3,4-Cl₂-5-CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3,4-Cl₂-5-CF₃ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3,4-Cl₂-5-CF₃ CF₃ H CH₂(D10-2a) 3,4-Cl₂-5-CF₃ CF₃ H CH₂(D32-1a) 3,4-Cl₂-5-CF₃ CF₃ C(O)CH₃ CH₂(D32-1a) 3,4-Cl₂-5-CF₃ CF₃ C(O)Et CH₂(D32-1a) 3,4-Cl₂-5-CF₃ CF₃ C(O)OCH₃ CH₂(D32-1a) 3,4-Cl₂-5-CF₃ CF₃ H CH═NOCH₃(Z) 3,4-Cl₂-5-CF₃ CF₃ CH₂OCH₃ CH═NOCH₃ 3,4-Cl₂-5-CF₃ CF₃ H CH═NOEt(Z) 3,4-Cl₂-5-CF₃ CF₃ C(O)Et C(O)OCH₃ 3,4-Cl₂-5-CF₃ CF₃ CH₂OC(O)CH₃ (D34-1c)Cl 3,4-Cl₂-5-CF₃ CF₃ C(O)CH₃ (D34-1c)Cl 3,4-Cl₂-5-CF₃ CF₃ C(O)Pr-c (D34-1c)Cl 3,4-Cl₂-5-CF₃ CF₃ C(O)OCH₃ (D34-1c)Cl 3,4-Cl₂-5-CF₃ CF₃ H (D34-1c)CN 3,4-Cl₂-5-CF₃ CF₃ CH₃ (D34-1c)CN 3,4-Cl₂-5-CF₃ CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3,4-Cl₂-5-CF₃ CF₃ C(O)Pr-i (D34-1c)CN 3,4-Cl₂-5-CF₃ CF₃ C(O)OCH₃ (D34-1c)CN 3,4-Cl₂-5-CF₃ CF₃ C(O)Et D34-3a 3,4-Cl₂-5-CF₃ CF₃ C(O)Pr-i D34-3a 3,4-Cl₂-5-CF₃ CF₂Cl C(O)OCH₃ CH₂OEt 3,4-Cl₂-5-CF₃ CF₂Cl H CH₂OCH₂CF₃ 3,4-Cl₂-5-CF₃ CF₂Cl H E4-1a 3,4-Cl₂-5-CF₃ CF₂Cl H CH₂C(O)NHCH₂CF₃ 3,4-Cl₂-5-CF₃ CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3,4-Cl₂-5-CF₃ CF₂Cl H CH₂(D10-2a) 3,4-Cl₂-5-CF₃ CF₂Cl H CH═NOCH₃(Z) 3,4-Cl₂-5-CF₃ CF₂Cl H CH═NOEt(Z) 3,4-Cl₂-5-CF₃ CF₂Cl C(O)Et C(O)OCH₃ 3,4-Cl₂-5-CF₃ CF₂Cl H (D34-1c)CN 3,5-(CF₃)₂-4-Cl CF₃ C(O)CH₃ CH₂CF₃ 3,5-(CF₃)₂-4-Cl CF₃ C(O)OCH₃ CH₂OCH₃ 3,5-(CF₃)₂-4-Cl CF₃ C(O)OCH₃ CH₂OEt 3,5-(CF₃)₂-4-Cl CF₃ H CH₂OCH₂CF₃ 3,5-(CF₃)₂-4-Cl CF₃ C(O)OCH₃ CH₂OCH₂CF₃ 3,5-(CF₃)₂-4-Cl CF₃ H E4-1a 3,5-(CF₃)₂-4-Cl CF₃ H CH₂C(O)NHCH₂CF₃ 3,5-(CF₃)₂-4-Cl CF₃ H CH(CH₃)C(O)NHCH₂CH₂Cl 3,5-(CF₃)₂-4-Cl CF₃ H CH(CH₃)C(O)NHCH₂CF₃ 3,5-(CF₃)₂-4-Cl CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3,5-(CF₃)₂-4-Cl CF₃ H CH₂(D10-2a) 3,5-(CF₃)₂-4-Cl CF₃ H CH₂(D32-1a) 3,5-(CF₃)₂-4-Cl CF₃ C(O)CH₃ CH₂(D32-1a) 3,5-(CF₃)₂-4-Cl CF₃ C(O)Et CH₂(D32-1a) 3,5-(CF₃)₂-4-Cl CF₃ C(O)OCH₃ CH₂(D32-1a) 3,5-(CF₃)₂-4-Cl CF₃ H CH═NOCH₃(Z) 3,5-(CF₃)₂-4-Cl CF₃ CH₂OCH₃ CH═NOCH₃ 3,5-(CF₃)₂-4-Cl CF₃ H CH═NOEt(Z) 3,5-(CF₃)₂-4-Cl CF₃ C(O)Et C(O)OCH₃ 3,5-(CF₃)₂-4-Cl CF₃ CH₂OC(O)CH₃ (D34-1c)Cl 3,5-(CF₃)₂-4-Cl CF₃ C(O)CH₃ (D34-1c)Cl 3,5-(CF₃)₂-4-Cl CF₃ C(O)Pr-c (D34-1c)Cl 3,5-(CF₃)₂-4-Cl CF₃ C(O)OCH₃ (D34-1c)Cl 3,5-(CF₃)₂-4-Cl CF₃ H (D34-1c)CN 3,5-(CF₃)₂-4-Cl CF₃ CH₃ (D34-1c)CN 3,5-(CF₃)₂-4-Cl CF₃ CH₂OC(O)CH₃ (D34-1c)CN 3,5-(CF₃)₂-4-Cl CF₃ C(O)Pr-i (D34-1c)CN 3,5-(CF₃)₂-4-Cl CF₃ C(O)OCH₃ (D34-1c)CN 3,5-(CF₃)₂-4-Cl CF₃ C(O)Et D34-3a 3,5-(CF₃)₂-4-Cl CF₃ C(O)Pr-i D34-3a 3,5-(CF₃)₂-4-Cl CF₂Cl C(O)OCH₃ CH₂OEt 3,5-(CF₃)₂-4-Cl CF₂Cl H CH₂OCH₂CF₃ 3,5-(CF₃)₂-4-Cl CF₂Cl H E4-1a 3,5-(CF₃)₂-4-Cl CF₂Cl H CH₂C(O)NHCH₂CF₃ 3,5-(CF₃)₂-4-Cl CF₂Cl H CH(CH₃)C(O)NHCH₂CF₃(D) 3,5-(CF₃)₂-4-Cl CF₂Cl H CH₂(D10-2a) 3,5-(CF₃)₂-4-Cl CF₂Cl H CH═NOCH₃(Z) 3,5-(CF₃)₂-4-Cl CF₂Cl H CH═NOEt(Z) 3,5-(CF₃)₂-4-Cl CF₂Cl C(O)Et C(O)OCH₃ 3,5-(CF₃)₂-4-Cl CF₂Cl H (D34-1c)CN 3,5-Cl₂-4-OCHF₂ CF₃ C(O)OCH₃ CH₂OEt 3,5-Cl₂-4-OCHF₂ CF₃ H CH₂OCH₂CF₃ 3,5-Cl₂-4-OCHF₂ CF₃ H E4-1a 3,5-Cl₂-4-OCHF₂ CF₃ H CH₂C(O)NHCH₂CF₃ 3,5-Cl₂-4-OCHF₂ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3,5-Cl₂-4-OCHF₂ CF₃ H CH₂(D10-2a) 3,5-Cl₂-4-OCHF₂ CF₃ H CH═NOCH₃(Z) 3,5-Cl₂-4-OCHF₂ CF₃ H CH═NOEt(Z) 3,5-Cl₂-4-OCHF₂ CF₃ C(O)Et C(O)OCH₃ 3,5-Cl₂-4-OCHF₂ CF₃ H (D34-1c)CN 3,5-Br₂-4-OCHF₂ CF₃ C(O)OCH₃ CH₂OEt 3,5-Br₂-4-OCHF₂ CF₃ H CH₂OCH₂CF₃ 3,5-Br₂-4-OCHF₂ CF₃ H E4-1a 3,5-Br₂-4-OCHF₂ CF₃ H CH₂C(O)NHCH₂CF₃ 3,5-Br₂-4-OCHF₂ CF₃ H CH(CH₃)C(O)NHCH₂CF₃(D) 3,5-Br₂-4-OCHF₂ CF₃ H CH₂(D10-2a) 3,5-Br₂-4-OCHF₂ CF₃ H CH═NOCH₃(Z) 3,5-Br₂-4-OCHF₂ CF₃ H CH═NOEt(Z) 3,5-Br₂-4-OCHF₂ CF₃ C(O)Et C(O)OCH₃ 3,5-Br₂-4-OCHF₂ CF₃ H (D34-1c)CN

Compounds represented by Structure Formulae [1]-1 to [1]-110 and [2]-1 to [2]-75 having structures in which G² is represented by G²-2-a.

In Table, the number representing the substitution site of the substituent (X)_(m) corresponds to the site indicated by the number in each of Structure Formulae [1]-1 to [1]-110 and [2]-1 to [2]-75.

Furthermore, in Table, aliphatic heterocyclic rings represented by E4-2a to E5-2c represent the following structures,

furthermore, in Table, T-1 represents the following structure,

in Table, the description of Et represents an ethyl group and, in the same manner, n-Pr and Pr-n represent normal propyl groups, i-Pr and Pr-i represent isopropyl groups, c-Pr and Pr-c represent cyclopropyl groups, i-Bu and Bu-i represent isobutyl groups, c-Bu and Bu-c represent cyclobutyl groups, and Ph represents a phenyl group.

TABLE 5 (X)_(m) R³ R^(4a) R^(2a) R^(1a) 3-Br CF₃ H H C(O)Pr-c 3-Br CF₃ H H C(O)CH₂Pr-c 3-Br CF₃ H H C(O)CH₂CF₃ 3-Br CF₃ CH₃ H C(O)(E4-2a) 3-Br CF₃ H H C(O)CH₂SCH₃ 3-Br CF₃ H H C(O)CH₂S(O)CH₃ 3-Br CF₃ H H C(O)CH₂SO₂CH₃ 3-Br CF₃ H H C(O)CH₂SEt 3-Br CF₃ H H C(O)CH₂S(O)Et 3-Br CF₃ H H C(O)CH₂SO₂Et 3-I CF₃ H H C(O)Et 3-I CF₃ H H C(O)Pr-n 3-I CF₃ H H C(O)Pr-i 3-I CF₃ H H C(O)Pr-c 3-I CF₃ CH₃ H C(O)Pr-c 3-I CF₃ H H C(O)Bu-i 3-I CF₃ H H C(O)CH₂Pr-c 3-I CF₃ CH₃ H C(O)CH₂Pr-c 3-I CF₃ H H C(O)CH₂CF₃ 3-I CF₃ CH₃ H C(O)CH₂CF₃ 3-I CF₃ CH₃ H C(O)(E4-2a) 3-I CF₃ H H C(O)CH₂SCH₃ 3-I CF₃ H H C(O)CH₂S(O)CH₃ 3-I CF₃ H H C(O)CH₂SO₂CH₃ 3-I CF₃ H H C(O)CH₂SEt 3-I CF₃ H H C(O)CH₂S(O)Et 3-I CF₃ H H C(O)CH₂SO₂Et 3-I CF₃ H H C(O)NHEt 3-I CF₃ H H C(O)NHPr-c 3-I CF₃ CH₃ H C(O)NHPr-c 3-CF₃ CF₃ H H C(O)Et 3-CF₃ CF₃ H H C(O)Pr-n 3-CF₃ CF₃ H H C(O)Pr-i 3-CF₃ CF₃ H H C(O)Pr-c 3-CF₃ CF₃ CH₃ H C(O)Pr-c 3-CF₃ CF₃ H H C(O)Bu-i 3-CF₃ CF₃ H H C(O)CH₂Pr-c 3-CF₃ CF₃ CH₃ H C(O)CH₂Pr-c 3-CF₃ CF₃ H H C(O)CH₂CF₃ 3-CF₃ CF₃ CH₃ H C(O)CH₂CF₃ 3-CF₃ CF₃ CH₃ H C(O)(E4-2a) 3-CF₃ CF₃ H H C(O)CH₂SCH₃ 3-CF₃ CF₃ H H C(O)CH₂S(O)CH₃ 3-CF₃ CF₃ H H C(O)CH₂SO₂CH₃ 3-CF₃ CF₃ H H C(O)CH₂SEt 3-CF₃ CF₃ H H C(O)CH₂S(O)Et 3-CF₃ CF₃ H H C(O)CH₂SO₂Et 3-CF₃ CF₃ H H C(O)NHEt 3-CF₃ CF₃ H H C(O)NHPr-c 3-CF₃ CF₃ CH₃ H C(O)NHPr-c 3-CF₂CF₃ CF₃ H H C(O)Pr-c 3-CF₂CF₃ CF₃ H H C(O)CH₂Pr-c 3-CF₂CF₃ CF₃ H H C(O)CH₂CF₃ 3-CF₂CF₃ CF₃ CH₃ H C(O)(E4-2a) 3-CF₂CF₃ CF₃ H H C(O)CH₂SCH₃ 3-CF₂CF₃ CF₃ H H C(O)CH₂S(O)CH₃ 3-CF₂CF₃ CF₃ H H C(O)CH₂SO₂CH₃ 3-CF₂CF₃ CF₃ H H C(O)CH₂SEt 3-CF₂CF₃ CF₃ H H C(O)CH₂S(O)Et 3-CF₂CF₃ CF₃ H H C(O)CH₂SO₂Et 3-OCF₃ CF₃ H H C(O)Pr-c 3-OCF₃ CF₃ H H C(O)CH₂Pr-c 3-OCF₃ CF₃ H H C(O)CH₂CF₃ 3-OCF₃ CF₃ CH₃ H C(O)(E4-2a) 3-OCF₃ CF₃ H H C(O)CH₂SCH₃ 3-OCF₃ CF₃ H H C(O)CH₂S(O)CH₃ 3-OCF₃ CF₃ H H C(O)CH₂SO₂CH₃ 3-OCF₃ CF₃ H H C(O)CH₂SEt 3-OCF₃ CF₃ H H C(O)CH₂S(O)Et 3-OCF₃ CF₃ H H C(O)CH₂SO₂Et 3-SCF₃ CF₃ H H C(O)Pr-c 3-SCF₃ CF₃ H H C(O)CH₂Pr-c 3-SCF₃ CF₃ H H C(O)CH₂CF₃ 3-SCF₃ CF₃ CH₃ H C(O)(E4-2a) 3-SCF₃ CF₃ H H C(O)CH₂SCH₃ 3-SCF₃ CF₃ H H C(O)CH₂S(O)CH₃ 3-SCF₃ CF₃ H H C(O)CH₂SO₂CH₃ 3-SCF₃ CF₃ H H C(O)CH₂SEt 3-SCF₃ CF₃ H H C(O)CH₂S(O)Et 3-SCF₃ CF₃ H H C(O)CH₂SO₂Et 3-SF₅ CF₃ H H C(O)Pr-c 3-SF₅ CF₃ H H C(O)CH₂Pr-c 3-SF₅ CF₃ H H C(O)CH₂CF₃ 3-SF₅ CF₃ CH₃ H C(O)(E4-2a) 3-SF₅ CF₃ H H C(O)CH₂SCH₃ 3-SF₅ CF₃ H H C(O)CH₂S(O)CH₃ 3-SF₅ CF₃ H H C(O)CH₂SO₂CH₃ 3-SF₅ CF₃ H H C(O)CH₂SEt 3-SF₅ CF₃ H H C(O)CH₂S(O)Et 3-SF₅ CF₃ H H C(O)CH₂SO₂Et 3-Cl-4-F CF₃ H H C(O)Et 3-Cl-4-F CF₃ H H C(O)Pr-n 3-Cl-4-F CF₃ H H C(O)Pr-i 3-Cl-4-F CF₃ H H C(O)Pr-c 3-Cl-4-F CF₃ CH₃ H C(O)Pr-c 3-Cl-4-F CF₃ H H C(O)Bu-i 3-Cl-4-F CF₃ H H C(O)CH₂Pr-c 3-Cl-4-F CF₃ CH₃ H C(O)CH₂Pr-c 3-Cl-4-F CF₃ H H C(O)CH₂CF₃ 3-Cl-4-F CF₃ CH₃ H C(O)CH₂CF₃ 3-Cl-4-F CF₃ CH₃ H C(O)(E4-2a) 3-Cl-4-F CF₃ H H C(O)CH₂SCH₃ 3-Cl-4-F CF₃ H H C(O)CH₂S(O)CH₃ 3-Cl-4-F CF₃ H H C(O)CH₂SO₂CH₃ 3-Cl-4-F CF₃ H H C(O)CH₂SEt 3-Cl-4-F CF₃ H H C(O)CH₂S(O)Et 3-Cl-4-F CF₃ H H C(O)CH₂SO₂Et 3-Cl-4-F CF₃ H H C(O)NHEt 3-Cl-4-F CF₃ H H C(O)NHPr-c 3-Cl-4-F CF₃ CH₃ H C(O)NHPr-c 3-F-5-Cl CF₃ H H C(O)Et 3-F-5-Cl CF₃ H H C(O)Pr-n 3-F-5-Cl CF₃ H H C(O)Pr-i 3-F-5-Cl CF₃ H H C(O)Pr-c 3-F-5-Cl CF₃ CH₃ H C(O)Pr-c 3-F-5-Cl CF₃ H H C(O)Bu-i 3-F-5-Cl CF₃ H H C(O)CH₂Pr-c 3-F-5-Cl CF₃ CH₃ H C(O)CH₂Pr-c 3-F-5-Cl CF₃ H H C(O)CH₂CF₃ 3-F-5-Cl CF₃ CH₃ H C(O)CH₂CF₃ 3-F-5-Cl CF₃ CH₃ H C(O)(E4-2a) 3-F-5-Cl CF₃ H H C(O)CH₂SCH₃ 3-F-5-Cl CF₃ H H C(O)CH₂S(O)CH₃ 3-F-5-Cl CF₃ H H C(O)CH₂SO₂CH₃ 3-F-5-Cl CF₃ H H C(O)CH₂SEt 3-F-5-Cl CF₃ H H C(O)CH₂S(O)Et 3-F-5-Cl CF₃ H H C(O)CH₂SO₂Et 3-F-5-Cl CF₃ H H C(O)NHEt 3-F-5-Cl CF₃ H H C(O)NHPr-c 3-F-5-Cl CF₃ CH₃ H C(O)NHPr-c 3,4-Cl₂ CF₃ H H C(O)Et 3,4-Cl₂ CF₃ H H C(O)Pr-n 3,4-Cl₂ CF₃ H H C(O)Pr-i 3,4-Cl₂ CF₃ H H C(O)Pr-c 3,4-Cl₂ CF₃ CH₃ H C(O)Pr-c 3,4-Cl₂ CF₃ H H C(O)Bu-i 3,4-Cl₂ CF₃ H H C(O)CH₂Pr-c 3,4-Cl₂ CF₃ CH₃ H C(O)CH₂Pr-c 3,4-Cl₂ CF₃ H H C(O)CH₂CF₃ 3,4-Cl₂ CF₃ CH₃ H C(O)CH₂CF₃ 3,4-Cl₂ CF₃ CH₃ H C(O)(E4-2a) 3,4-Cl₂ CF₃ H H C(O)CH₂SCH₃ 3,4-Cl₂ CF₃ H H C(O)CH₂S(O)CH₃ 3,4-Cl₂ CF₃ H H C(O)CH₂SO₂CH₃ 3,4-Cl₂ CF₃ H H C(O)CH₂SEt 3,4-Cl₂ CF₃ H H C(O)CH₂S(O)Et 3,4-Cl₂ CF₃ H H C(O)CH₂SO₂Et 3,4-Cl₂ CF₃ H H C(O)NHEt 3,4-Cl₂ CF₃ H H C(O)NHPr-c 3,4-Cl₂ CF₃ CH₃ H C(O)NHPr-c 3,5-Cl₂ CF₃ H H C(O)CH₃ 3,5-Cl₂ CF₃ H H C(O)Et 3,5-Cl₂ CF₃ CH₃ H C(O)Et 3,5-Cl₂ CF₃ H Et C(O)Et 3,5-Cl₂ CF₃ H CH₂C≡CH C(O)Et 3,5-Cl₂ CF₃ H H C(O)Pr-n 3,5-Cl₂ CF₃ CH₃ H C(O)Pr-n 3,5-Cl₂ CF₃ H Et C(O)Pr-n 3,5-Cl₂ CF₃ H H C(O)Pr-i 3,5-Cl₂ CF₃ CH₃ H C(O)Pr-i 3,5-Cl₂ CF₃ H H C(O)Pr-c 3,5-Cl₂ CF₃ CH₃ H C(O)Pr-c 3,5-Cl₂ CF₃ H Et C(O)Pr-c 3,5-Cl₂ CF₃ CH₃ Et C(O)Pr-c 3,5-Cl₂ CF₃ H CH₂Pr-c C(O)Pr-c 3,5-Cl₂ CF₃ H CH₂OCH₃ C(O)Pr-c 3,5-Cl₂ CF₃ CH₃ CH₂CN C(O)Pr-c 3,5-Cl₂ CF₃ H CH₂C≡CH C(O)Pr-c 3,5-Cl₂ CF₃ CH₃ CH₂C≡CH C(O)Pr-c 3,5-Cl₂ CF₃ H H C(O)Bu-i 3,5-Cl₂ CF₃ CH₃ H C(O)Bu-i 3,5-Cl₂ CF₃ H H C(O)CH₂Pr-c 3,5-Cl₂ CF₃ CH₃ H C(O)CH₂Pr-c 3,5-Cl₂ CF₃ CN H C(O)CH₂Pr-c 3,5-Cl₂ CF₃ H Et C(O)CH₂Pr-c 3,5-Cl₂ CF₃ H H C(O)CH₂CF₃ 3,5-Cl₂ CF₃ CH₃ H C(O)CH₂CF₃ 3,5-Cl₂ CF₃ H H C(O)(E4-2a) 3,5-Cl₂ CF₃ CH₃ H C(O)(E4-2a) 3,5-Cl₂ CF₃ H H C(O)CH₂SCH₃ 3,5-Cl₂ CF₃ H H C(O)CH₂S(O)CH₃ 3,5-Cl₂ CF₃ H H C(O)CH₂SO₂CH₃ 3,5-Cl₂ CF₃ H H C(O)CH₂SEt 3,5-Cl₂ CF₃ H Et C(O)CH₂SEt 3,5-Cl₂ CF₃ H H C(O)CH₂S(O)Et 3,5-Cl₂ CF₃ H H C(O)CH₂SO₂Et 3,5-Cl₂ CF₃ H CH₃ C(O)CH₂SO₂Et 3,5-Cl₂ CF₃ H H C(O)NHEt 3,5-Cl₂ CF₃ CH₃ H C(O)NHEt 3,5-Cl₂ CF₃ H H C(O)NHPr-c 3,5-Cl₂ CF₃ CH₃ H C(O)NHPr-c 3,5-Cl₂ CF₃ CH₃ H C(O)NHCH₂C≡CH 3,5-Cl₂ CF₂Cl H H C(O)Pr-c 3,5-Cl₂ CF₂Cl H H C(O)CH₂Pr-c 3,5-Cl₂ CF₂Cl H H C(O)CH₂CF₃ 3,5-Cl₂ CF₂Cl CH₃ H C(O)(E4-2a) 3,5-Cl₂ CF₂Cl H H C(O)CH₂SCH₃ 3,5-Cl₂ CF₂Cl H H C(O)CH₂S(O)CH₃ 3,5-Cl₂ CF₂Cl H H C(O)CH₂SO₂CH₃ 3,5-Cl₂ CF₂Cl H H C(O)CH₂SEt 3,5-Cl₂ CF₂Cl H H C(O)CH₂S(O)Et 3,5-Cl₂ CF₂Cl H H C(O)CH₂SO₂Et 3-Br-4-F CF₃ H H C(O)Et 3-Br-4-F CF₃ H H C(O)Pr-n 3-Br-4-F CF₃ H H C(O)Pr-i 3-Br-4-F CF₃ H H C(O)Pr-c 3-Br-4-F CF₃ CH₃ H C(O)Pr-c 3-Br-4-F CF₃ H H C(O)Bu-i 3-Br-4-F CF₃ H H C(O)CH₂Pr-c 3-Br-4-F CF₃ CH₃ H C(O)CH₂Pr-c 3-Br-4-F CF₃ H H C(O)CH₂CF₃ 3-Br-4-F CF₃ CH₃ H C(O)CH₂CF₃ 3-Br-4-F CF₃ CH₃ H C(O)(E4-2a) 3-Br-4-F CF₃ H H C(O)CH₂SCH₃ 3-Br-4-F CF₃ H H C(O)CH₂S(O)CH₃ 3-Br-4-F CF₃ H H C(O)CH₂SO₂CH₃ 3-Br-4-F CF₃ H H C(O)CH₂SEt 3-Br-4-F CF₃ H H C(O)CH₂S(O)Et 3-Br-4-F CF₃ H H C(O)CH₂SO₂Et 3-Br-4-F CF₃ H H C(O)NHEt 3-Br-4-F CF₃ H H C(O)NHPr-c 3-Br-4-F CF₃ CH₃ H C(O)NHPr-c 3-F-5-Br CF₃ H H C(O)Et 3-F-5-Br CF₃ H H C(O)Pr-n 3-F-5-Br CF₃ H H C(O)Pr-i 3-F-5-Br CF₃ H H C(O)Pr-c 3-F-5-Br CF₃ CH₃ H C(O)Pr-c 3-F-5-Br CF₃ H H C(O)Bu-i 3-F-5-Br CF₃ H H C(O)CH₂Pr-c 3-F-5-Br CF₃ CH₃ H C(O)CH₂Pr-c 3-F-5-Br CF₃ H H C(O)CH₂CF₃ 3-F-5-Br CF₃ CH₃ H C(O)CH₂CF₃ 3-F-5-Br CF₃ CH₃ H C(O)(E4-2a) 3-F-5-Br CF₃ H H C(O)CH₂SCH₃ 3-F-5-Br CF₃ H H C(O)CH₂S(O)CH₃ 3-F-5-Br CF₃ H H C(O)CH₂SO₂CH₃ 3-F-5-Br CF₃ H H C(O)CH₂SEt 3-F-5-Br CF₃ H H C(O)CH₂S(O)Et 3-F-5-Br CF₃ H H C(O)CH₂SO₂Et 3-F-5-Br CF₃ H H C(O)NHEt 3-F-5-Br CF₃ H H C(O)NHPr-c 3-F-5-Br CF₃ CH₃ H C(O)NHPr-c 3-Br-4-Cl CF₃ H H C(O)Pr-c 3-Br-4-Cl CF₃ H H C(O)CH₂Pr-c 3-Br-4-Cl CF₃ H H C(O)CH₂CF₃ 3-Br-4-Cl CF₃ CH₃ H C(O)(E4-2a) 3-Br-4-Cl CF₃ H H C(O)CH₂SCH₃ 3-Br-4-Cl CF₃ H H C(O)CH₂S(O)CH₃ 3-Br-4-Cl CF₃ H H C(O)CH₂SO₂CH₃ 3-Br-4-Cl CF₃ H H C(O)CH₂SEt 3-Br-4-Cl CF₃ H H C(O)CH₂S(O)Et 3-Br-4-Cl CF₃ H H C(O)CH₂SO₂Et 3-Cl-4-Br CF₃ H H C(O)Pr-c 3-Cl-4-Br CF₃ H H C(O)CH₂Pr-c 3-Cl-4-Br CF₃ H H C(O)CH₂CF₃ 3-Cl-4-Br CF₃ CH₃ H C(O)(E4-2a) 3-Cl-4-Br CF₃ H H C(O)CH₂SCH₃ 3-Cl-4-Br CF₃ H H C(O)CH₂S(O)CH₃ 3-Cl-4-Br CF₃ H H C(O)CH₂SO₂CH₃ 3-Cl-4-Br CF₃ H H C(O)CH₂SEt 3-Cl-4-Br CF₃ H H C(O)CH₂S(O)Et 3-Cl-4-Br CF₃ H H C(O)CH₂SO₂Et 3-Cl-5-Br CF₃ H H C(O)CH₃ 3-Cl-5-Br CF₃ H H C(O)Et 3-Cl-5-Br CF₃ CH₃ H C(O)Et 3-Cl-5-Br CF₃ H Et C(O)Et 3-Cl-5-Br CF₃ H CH₂C≡CH C(O)Et 3-Cl-5-Br CF₃ H H C(O)Pr-n 3-Cl-5-Br CF₃ CH₃ H C(O)Pr-n 3-Cl-5-Br CF₃ H Et C(O)Pr-n 3-Cl-5-Br CF₃ H H C(O)Pr-i 3-Cl-5-Br CF₃ CH₃ H C(O)Pr-i 3-Cl-5-Br CF₃ H H C(O)Pr-c 3-Cl-5-Br CF₃ CH₃ H C(O)Pr-c 3-Cl-5-Br CF₃ H Et C(O)Pr-c 3-Cl-5-Br CF₃ CH₃ Et C(O)Pr-c 3-Cl-5-Br CF₃ H CH₂Pr-c C(O)Pr-c 3-Cl-5-Br CF₃ H CH₂OCH₃ C(O)Pr-c 3-Cl-5-Br CF₃ CH₃ CH₂CN C(O)Pr-c 3-Cl-5-Br CF₃ H CH₂C≡CH C(O)Pr-c 3-Cl-5-Br CF₃ CH₃ CH₂C≡CH C(O)Pr-c 3-Cl-5-Br CF₃ H H C(O)Bu-i 3-Cl-5-Br CF₃ CH₃ H C(O)Bu-i 3-Cl-5-Br CF₃ H H C(O)CH₂Pr-c 3-Cl-5-Br CF₃ CH₃ H C(O)CH₂Pr-c 3-Cl-5-Br CF₃ CN H C(O)CH₂Pr-c 3-Cl-5-Br CF₃ H Et C(O)CH₂Pr-c 3-Cl-5-Br CF₃ H H C(O)CH₂CF₃ 3-Cl-5-Br CF₃ CH₃ H C(O)CH₂CF₃ 3-Cl-5-Br CF₃ H H C(O)(E4-2a) 3-Cl-5-Br CF₃ CH₃ H C(O)(E4-2a) 3-Cl-5-Br CF₃ H H C(O)CH₂SCH₃ 3-Cl-5-Br CF₃ H H C(O)CH₂S(O)CH₃ 3-Cl-5-Br CF₃ H H C(O)CH₂SO₂CH₃ 3-Cl-5-Br CF₃ H H C(O)CH₂SEt 3-Cl-5-Br CF₃ H Et C(O)CH₂SEt 3-Cl-5-Br CF₃ H H C(O)CH₂S(O)Et 3-Cl-5-Br CF₃ H H C(O)CH₂SO₂Et 3-Cl-5-Br CF₃ H CH₃ C(O)CH₂SO₂Et 3-Cl-5-Br CF₃ H H C(O)NHEt 3-Cl-5-Br CF₃ CH₃ H C(O)NHEt 3-Cl-5-Br CF₃ H H C(O)NHPr-c 3-Cl-5-Br CF₃ CH₃ H C(O)NHPr-c 3-Cl-5-Br CF₃ CH₃ H C(O)NHCH₂C≡CH 3-Cl-5-Br CF₂Cl H H C(O)Pr-c 3-Cl-5-Br CF₂Cl H H C(O)CH₂Pr-c 3-Cl-5-Br CF₂Cl H H C(O)CH₂CF₃ 3-Cl-5-Br CF₂Cl CH₃ H C(O)(E4-2a) 3-Cl-5-Br CF₂Cl H H C(O)CH₂SCH₃ 3-Cl-5-Br CF₂Cl H H C(O)CH₂S(O)CH₃ 3-Cl-5-Br CF₂Cl H H C(O)CH₂SO₂CH₃ 3-Cl-5-Br CF₂Cl H H C(O)CH₂SEt 3-Cl-5-Br CF₂Cl H H C(O)CH₂S(O)Et 3-Cl-5-Br CF₂Cl H H C(O)CH₂SO₂Et 3,4-Br₂ CF₃ H H C(O)Pr-c 3,4-Br₂ CF₃ H H C(O)CH₂Pr-c 3,4-Br₂ CF₃ H H C(O)CH₂CF₃ 3,4-Br₂ CF₃ CH₃ H C(O)(E4-2a) 3,4-Br₂ CF₃ H H C(O)CH₂SCH₃ 3,4-Br₂ CF₃ H H C(O)CH₂S(O)CH₃ 3,4-Br₂ CF₃ H H C(O)CH₂SO₂CH₃ 3,4-Br₂ CF₃ H H C(O)CH₂SEt 3,4-Br₂ CF₃ H H C(O)CH₂S(O)Et 3,4-Br₂ CF₃ H H C(O)CH₂SO₂Et 3,5-Br₂ CF₃ H H C(O)CH₃ 3,5-Br₂ CF₃ H H C(O)Et 3,5-Br₂ CF₃ CH₃ H C(O)Et 3,5-Br₂ CF₃ H Et C(O)Et 3,5-Br₂ CF₃ H CH₂C≡CH C(O)Et 3,5-Br₂ CF₃ H H C(O)Pr-n 3,5-Br₂ CF₃ CH₃ H C(O)Pr-n 3,5-Br₂ CF₃ H Et C(O)Pr-n 3,5-Br₂ CF₃ H H C(O)Pr-i 3,5-Br₂ CF₃ CH₃ H C(O)Pr-i 3,5-Br₂ CF₃ H H C(O)Pr-c 3,5-Br₂ CF₃ CH₃ H C(O)Pr-c 3,5-Br₂ CF₃ H Et C(O)Pr-c 3,5-Br₂ CF₃ CH₃ Et C(O)Pr-c 3,5-Br₂ CF₃ H CH₂Pr-c C(O)Pr-c 3,5-Br₂ CF₃ H CH₂OCH₃ C(O)Pr-c 3,5-Br₂ CF₃ CH₃ CH₂CN C(O)Pr-c 3,5-Br₂ CF₃ H CH₂C≡H C(O)Pr-c 3,5-Br₂ CF₃ CH₃ CH₂C≡CH C(O)Pr-c 3,5-Br₂ CF₃ H H C(O)Bu-i 3,5-Br₂ CF₃ CH₃ H C(O)Bu-i 3,5-Br₂ CF₃ H H C(O)CH₂Pr-c 3,5-Br₂ CF₃ CH₃ H C(O)CH₂Pr-c 3,5-Br₂ CF₃ CN H C(O)CH₂Pr-c 3,5-Br₂ CF₃ H Et C(O)CH₂Pr-c 3,5-Br₂ CF₃ H H C(O)CH₂CF₃ 3,5-Br₂ CF₃ CH₃ H C(O)CH₂CF₃ 3,5-Br₂ CF₃ H H C(O)(E4-2a) 3,5-Br₂ CF₃ CH₃ H C(O)(E4-2a) 3,5-Br₂ CF₃ H H C(O)CH₂SCH₃ 3,5-Br₂ CF₃ H H C(O)CH₂S(O)CH₃ 3,5-Br₂ CF₃ H H C(O)CH₂SO₂CH₃ 3,5-Br₂ CF₃ H H C(O)CH₂SEt 3,5-Br₂ CF₃ H Et C(O)CH₂SEt 3,5-Br₂ CF₃ H H C(O)CH₂S(O)Et 3,5-Br₂ CF₃ H H C(O)CH₂SO₂Et 3,5-Br₂ CF₃ H CH₃ C(O)CH₂SO₂Et 3,5-Br₂ CF₃ H H C(O)NHEt 3,5-Br₂ CF₃ CH₃ H C(O)NHEt 3,5-Br₂ CF₃ H H C(O)NHPr-c 3,5-Br₂ CF₃ CH₃ H C(O)NHPr-c 3,5-Br₂ CF₃ CH₃ H C(O)NHCH₂C≡CH 3,5-Br₂ CF₂Cl H H C(O)Pr-c 3,5-Br₂ CF₂Cl H H C(O)CH₂Pr-c 3,5-Br₂ CF₂Cl H H C(O)CH₂CF₃ 3,5-Br₂ CF₂Cl CH₃ H C(O)(E4-2a) 3,5-Br₂ CF₂Cl H H C(O)CH₂SCH₃ 3,5-Br₂ CF₂Cl H H C(O)CH₂S(O)CH₃ 3,5-Br₂ CF₂Cl H H C(O)CH₂SO₂CH₃ 3,5-Br₂ CF₂Cl H H C(O)CH₂SEt 3,5-Br₂ CF₂Cl H H C(O)CH₂S(O)Et 3,5-Br₂ CF₂Cl H H C(O)CH₂SO₂Et 3-I-4-F CF₃ H H C(O)Pr-c 3-I-4-F CF₃ H H C(O)CH₂Pr-c 3-I-4-F CF₃ H H C(O)CH₂CF₃ 3-I-4-F CF₃ CH₃ H C(O)(E4-2a) 3-I-4-F CF₃ H H C(O)CH₂SCH₃ 3-I-4-F CF₃ H H C(O)CH₂S(O)CH₃ 3-I-4-F CF₃ H H C(O)CH₂SO₂CH₃ 3-I-4-F CF₃ H H C(O)CH₂SEt 3-I-4-F CF₃ H H C(O)CH₂S(O)Et 3-I-4-F CF₃ H H C(O)CH₂SO₂Et 3-F-5-I CF₃ H H C(O)Pr-c 3-F-5-I CF₃ H H C(O)CH₂Pr-c 3-F-5-I CF₃ H H C(O)CH₂CF₃ 3-F-5-I CF₃ CH₃ H C(O)(E4-2a) 3-F-5-I CF₃ H H C(O)CH₂SCH₃ 3-F-5-I CF₃ H H C(O)CH₂S(O)CH₃ 3-F-5-I CF₃ H H C(O)CH₂SO₂CH₃ 3-F-5-I CF₃ H H C(O)CH₂SEt 3-F-5-I CF₃ H H C(O)CH₂S(O)Et 3-F-5-I CF₃ H H C(O)CH₂SO₂Et 3-Cl-5-I CF₃ H H C(O)Et 3-Cl-5-I CF₃ H H C(O)Pr-n 3-Cl-5-I CF₃ H H C(O)Pr-i 3-Cl-5-I CF₃ H H C(O)Pr-c 3-Cl-5-I CF₃ CH₃ H C(O)Pr-c 3-Cl-5-I CF₃ H H C(O)Bu-i 3-Cl-5-I CF₃ H H C(O)CH₂Pr-c 3-Cl-5-I CF₃ CH₃ H C(O)CH₂Pr-c 3-Cl-5-I CF₃ H H C(O)CH₂CF₃ 3-Cl-5-I CF₃ CH₃ H C(O)CH₂CF₃ 3-Cl-5-I CF₃ CH₃ H C(O)(E4-2a) 3-Cl-5-I CF₃ H H C(O)CH₂SCH₃ 3-Cl-5-I CF₃ H H C(O)CH₂S(O)CH₃ 3-Cl-5-I CF₃ H H C(O)CH₂SO₂CH₃ 3-Cl-5-I CF₃ H H C(O)CH₂SEt 3-Cl-5-I CF₃ H H C(O)CH₂S(O)Et 3-Cl-5-I CF₃ H H C(O)CH₂SO₂Et 3-Cl-5-I CF₃ H H C(O)NHEt 3-Cl-5-I CF₃ H H C(O)NHPr-c 3-Cl-5-I CF₃ CH₃ H C(O)NHPr-c 3-CF₃-4-F CF₃ H H C(O)Et 3-CF₃-4-F CF₃ H H C(O)Pr-n 3-CF₃-4-F CF₃ H H C(O)Pr-i 3-CF₃-4-F CF₃ H H C(O)Pr-c 3-CF₃-4-F CF₃ CH₃ H C(O)Pr-c 3-CF₃-4-F CF₃ H H C(O)Bu-i 3-CF₃-4-F CF₃ H H C(O)CH₂Pr-c 3-CF₃-4-F CF₃ CH₃ H C(O)CH₂Pr-c 3-CF₃-4-F CF₃ H H C(O)CH₂CF₃ 3-CF₃-4-F CF₃ CH₃ H C(O)CH₂CF₃ 3-CF₃-4-F CF₃ CH₃ H C(O)(E4-2a) 3-CF₃-4-F CF₃ H H C(O)CH₂SCH₃ 3-CF₃-4-F CF₃ H H C(O)CH₂S(O)CH₃ 3-CF₃-4-F CF₃ H H C(O)CH₂SO₂CH₃ 3-CF₃-4-F CF₃ H H C(O)CH₂SEt 3-CF₃-4-F CF₃ H H C(O)CH₂S(O)Et 3-CF₃-4-F CF₃ H H C(O)CH₂SO₂Et 3-CF₃-4-F CF₃ H H C(O)NHEt 3-CF₃-4-F CF₃ H H C(O)NHPr-c 3-CF₃-4-F CF₃ CH₃ H C(O)NHPr-c 3-F-5-CF₃ CF₃ H H C(O)Et 3-F-5-CF₃ CF₃ H H C(O)Pr-n 3-F-5-CF₃ CF₃ H H C(O)Pr-i 3-F-5-CF₃ CF₃ H H C(O)Pr-c 3-F-5-CF₃ CF₃ CH₃ H C(O)Pr-c 3-F-5-CF₃ CF₃ H H C(O)Bu-i 3-F-5-CF₃ CF₃ H H C(O)CH₂Pr-c 3-F-5-CF₃ CF₃ CH₃ H C(O)CH₂Pr-c 3-F-5-CF₃ CF₃ H H C(O)CH₂CF₃ 3-F-5-CF₃ CF₃ CH₃ H C(O)CH₂CF₃ 3-F-5-CF₃ CF₃ CH₃ H C(O)(E4-2a) 3-F-5-CF₃ CF₃ H H C(O)CH₂SCH₃ 3-F-5-CF₃ CF₃ H H C(O)CH₂S(O)CH₃ 3-F-5-CF₃ CF₃ H H C(O)CH₂SO₂CH₃ 3-F-5-CF₃ CF₃ H H C(O)CH₂SEt 3-F-5-CF₃ CF₃ H H C(O)CH₂S(O)Et 3-F-5-CF₃ CF₃ H H C(O)CH₂SO₂Et 3-F-5-CF₃ CF₃ H H C(O)NHEt 3-F-5-CF₃ CF₃ H H C(O)NHPr-c 3-F-5-CF₃ CF₃ CH₃ H C(O)NHPr-c 3-CF₃-4-Cl CF₃ H H C(O)Et 3-CF₃-4-Cl CF₃ H H C(O)Pr-n 3-CF₃-4-Cl CF₃ H H C(O)Pr-i 3-CF₃-4-Cl CF₃ H H C(O)Pr-c 3-CF₃-4-Cl CF₃ CH₃ H C(O)Pr-c 3-CF₃-4-Cl CF₃ H H C(O)Bu-i 3-CF₃-4-Cl CF₃ H H C(O)CH₂Pr-c 3-CF₃-4-Cl CF₃ CH₃ H C(O)CH₂Pr-c 3-CF₃-4-Cl CF₃ H H C(O)CH₂CF₃ 3-CF₃-4-Cl CF₃ CH₃ H C(O)CH₂CF₃ 3-CF₃-4-Cl CF₃ CH₃ H C(O)(E4-2a) 3-CF₃-4-Cl CF₃ H H C(O)CH₂SCH₃ 3-CF₃-4-Cl CF₃ H H C(O)CH₂S(O)CH₃ 3-CF₃-4-Cl CF₃ H H C(O)CH₂SO₂CH₃ 3-CF₃-4-Cl CF₃ H H C(O)CH₂SEt 3-CF₃-4-Cl CF₃ H H C(O)CH₂S(O)Et 3-CF₃-4-Cl CF₃ H H C(O)CH₂SO₂Et 3-CF₃-4-Cl CF₃ H H C(O)NHEt 3-CF₃-4-Cl CF₃ H H C(O)NHPr-c 3-CF₃-4-Cl CF₃ CH₃ H C(O)NHPr-c 3-Cl-5-CF₃ CF₃ H H C(O)CH₃ 3-Cl-5-CF₃ CF₃ H H C(O)Et 3-Cl-5-CF₃ CF₃ CH₃ H C(O)Et 3-Cl-5-CF₃ CF₃ H Et C(O)Et 3-Cl-5-CF₃ CF₃ H CH₂C≡CH C(O)Et 3-Cl-5-CF₃ CF₃ H H C(O)Pr-n 3-Cl-5-CF₃ CF₃ CH₃ H C(O)Pr-n 3-Cl-5-CF₃ CF₃ H Et C(O)Pr-n 3-Cl-5-CF₃ CF₃ H H C(O)Pr-i 3-Cl-5-CF₃ CF₃ CH₃ H C(O)Pr-i 3-Cl-5-CF₃ CF₃ H H C(O)Pr-c 3-Cl-5-CF₃ CF₃ CH₃ H C(O)Pr-c 3-Cl-5-CF₃ CF₃ H Et C(O)Pr-c 3-Cl-5-CF₃ CF₃ CH₃ Et C(O)Pr-c 3-Cl-5-CF₃ CF₃ H CH₂Pr-c C(O)Pr-c 3-Cl-5-CF₃ CF₃ H CH₂OCH₃ C(O)Pr-c 3-Cl-5-CF₃ CF₃ CH₃ CH₂CN C(O)Pr-c 3-Cl-5-CF₃ CF₃ H CH₂C≡CH C(O)Pr-c 3-Cl-5-CF₃ CF₃ CH₃ CH₂C≡CH C(O)Pr-c 3-Cl-5-CF₃ CF₃ H H C(O)Bu-i 3-Cl-5-CF₃ CF₃ CH₃ H C(O)Bu-i 3-Cl-5-CF₃ CF₃ H H C(O)CH₂Pr-c 3-Cl-5-CF₃ CF₃ CH₃ H C(O)CH₂Pr-c 3-Cl-5-CF₃ CF₃ CN H C(O)CH₂Pr-c 3-Cl-5-CF₃ CF₃ H Et C(O)CH₂Pr-c 3-Cl-5-CF₃ CF₃ H H C(O)CH₂CF₃ 3-Cl-5-CF₃ CF₃ CH₃ H C(O)CH₂CF₃ 3-Cl-5-CF₃ CF₃ H H C(O)(E4-2a) 3-Cl-5-CF₃ CF₃ CH₃ H C(O)(E4-2a) 3-Cl-5-CF₃ CF₃ H H C(O)CH₂SCH₃ 3-Cl-5-CF₃ CF₃ H H C(O)CH₂S(O)CH₃ 3-Cl-5-CF₃ CF₃ H H C(O)CH₂SO₂CH₃ 3-Cl-5-CF₃ CF₃ H H C(O)CH₂SEt 3-Cl-5-CF₃ CF₃ H Et C(O)CH₂SEt 3-Cl-5-CF₃ CF₃ H H C(O)CH₂S(O)Et 3-Cl-5-CF₃ CF₃ H H C(O)CH₂SO₂Et 3-Cl-5-CF₃ CF₃ H CH₃ C(O)CH₂SO₂Et 3-Cl-5-CF₃ CF₃ H H C(O)NHEt 3-Cl-5-CF₃ CF₃ CH₃ H C(O)NHEt 3-Cl-5-CF₃ CF₃ H H C(O)NHPr-c 3-Cl-5-CF₃ CF₃ CH₃ H C(O)NHPr-c 3-Cl-5-CF₃ CF₃ CH₃ H C(O)NHCH₂C≡CH 3-Cl-5-CF₃ CF₂Cl H H C(O)Pr-c 3-Cl-5-CF₃ CF₂Cl H H C(O)CH₂Pr-c 3-Cl-5-CF₃ CF₂Cl H H C(O)CH₂CF₃ 3-Cl-5-CF₃ CF₂Cl CH₃ H C(O)(E4-2a) 3-Cl-5-CF₃ CF₂Cl H H C(O)CH₂SCH₃ 3-Cl-5-CF₃ CF₂Cl H H C(O)CH₂S(O)CH₃ 3-Cl-5-CF₃ CF₂Cl H H C(O)CH₂SO₂CH₃ 3-Cl-5-CF₃ CF₂Cl H H C(O)CH₂SEt 3-Cl-5-CF₃ CF₂Cl H H C(O)CH₂S(O)Et 3-Cl-5-CF₃ CF₂Cl H H C(O)CH₂SO₂Et 3-Br-5-CF₃ CF₃ H H C(O)CH₃ 3-Br-5-CF₃ CF₃ H H C(O)Et 3-Br-5-CF₃ CF₃ CH₃ H C(O)Et 3-Br-5-CF₃ CF₃ H Et C(O)Et 3-Br-5-CF₃ CF₃ H CH₂C≡CH C(O)Et 3-Br-5-CF₃ CF₃ H H C(O)Pr-n 3-Br-5-CF₃ CF₃ CH₃ H C(O)Pr-n 3-Br-5-CF₃ CF₃ H Et C(O)Pr-n 3-Br-5-CF₃ CF₃ H H C(O)Pr-i 3-Br-5-CF₃ CF₃ CH₃ H C(O)Pr-i 3-Br-5-CF₃ CF₃ H H C(O)Pr-c 3-Br-5-CF₃ CF₃ CH₃ H C(O)Pr-c 3-Br-5-CF₃ CF₃ H Et C(O)Pr-c 3-Br-5-CF₃ CF₃ CH₃ Et C(O)Pr-c 3-Br-5-CF₃ CF₃ H CH₂Pr-c C(O)Pr-c 3-Br-5-CF₃ CF₃ H CH₂OCH₃ C(O)Pr-c 3-Br-5-CF₃ CF₃ CH₃ CH₂CN C(O)Pr-c 3-Br-5-CF₃ CF₃ H CH₂C≡CH C(O)Pr-c 3-Br-5-CF₃ CF₃ CH₃ CH₂C≡CH C(O)Pr-c 3-Br-5-CF₃ CF₃ H H C(O)Bu-i 3-Br-5-CF₃ CF₃ CH₃ H C(O)Bu-i 3-Br-5-CF₃ CF₃ H H C(O)CH₂Pr-c 3-Br-5-CF₃ CF₃ CH₃ H C(O)CH₂Pr-c 3-Br-5-CF₃ CF₃ CN H C(O)CH₂Pr-c 3-Br-5-CF₃ CF₃ H Et C(O)CH₂Pr-c 3-Br-5-CF₃ CF₃ H H C(O)CH₂CF₃ 3-Br-5-CF₃ CF₃ CH₃ H C(O)CH₂CF₃ 3-Br-5-CF₃ CF₃ H H C(O)(E4-2a) 3-Br-5-CF₃ CF₃ CH₃ H C(O)(E4-2a) 3-Br-5-CF₃ CF₃ H H C(O)CH₂SCH₃ 3-Br-5-CF₃ CF₃ H H C(O)CH₂S(O)CH₃ 3-Br-5-CF₃ CF₃ H H C(O)CH₂SO₂CH₃ 3-Br-5-CF₃ CF₃ H H C(O)CH₂SEt 3-Br-5-CF₃ CF₃ H Et C(O)CH₂SEt 3-Br-5-CF₃ CF₃ H H C(O)CH₂S(O)Et 3-Br-5-CF₃ CF₃ H H C(O)CH₂SO₂Et 3-Br-5-CF₃ CF₃ H CH₃ C(O)CH₂SO₂Et 3-Br-5-CF₃ CF₃ H H C(O)NHEt 3-Br-5-CF₃ CF₃ CH₃ H C(O)NHEt 3-Br-5-CF₃ CF₃ H H C(O)NHPr-c 3-Br-5-CF₃ CF₃ CH₃ H C(O)NHPr-c 3-Br-5-CF₃ CF₃ CH₃ H C(O)NHCH₂C≡CH 3-Br-5-CF₃ CF₂Cl H H C(O)Pr-c 3-Br-5-CF₃ CF₂Cl H H C(O)CH₂Pr-c 3-Br-5-CF₃ CF₂Cl H H C(O)CH₂CF₃ 3-Br-5-CF₃ CF₂Cl CH₃ H C(O)(E4-2a) 3-Br-5-CF₃ CF₂Cl H H C(O)CH₂SCH₃ 3-Br-5-CF₃ CF₂Cl H H C(O)CH₂S(O)CH₃ 3-Br-5-CF₃ CF₂Cl H H C(O)CH₂SO₂CH₃ 3-Br-5-CF₃ CF₂Cl H H C(O)CH₂SEt 3-Br-5-CF₃ CF₂Cl H H C(O)CH₂S(O)Et 3-Br-5-CF₃ CF₂Cl H H C(O)CH₂SO₂Et 3,5-(CF₃)₂ CF₃ H H C(O)CH₃ 3,5-(CF₃)₂ CF₃ H H C(O)Et 3,5-(CF₃)₂ CF₃ CH₃ H C(O)Et 3,5-(CF₃)₂ CF₃ CH₃(S) H C(O)Et 3,5-(CF₃)₂ CF₃ CN H C(O)Et 3,5-(CF₃)₂ CF₃ H Et C(O)Et 3,5-(CF₃)₂ CF₃ H CH₂CN C(O)Et 3,5-(CF₃)₂ CF₃ H CH₂CH≡CH₂ C(O)Et 3,5-(CF₃)₂ CF₃ H CH₂C≡CH C(O)Et 3,5-(CF₃)₂ CF₃ H H C(O)Pr-n 3,5-(CF₃)₂ CF₃ CH₃ H C(O)Pr-n 3,5-(CF₃)₂ CF₃ CH₃(S) H C(O)Pr-n 3,5-(CF₃)₂ CF₃ H Et C(O)Pr-n 3,5-(CF₃)₂ CF₃ H H C(O)Pr-i 3,5-(CF₃)₂ CF₃ CH₃ H C(O)Pr-i 3,5-(CF₃)₂ CF₃ CH₃(S) H C(O)Pr-i 3,5-(CF₃)₂ CF₃ CN H C(O)Pr-i 3,5-(CF₃)₂ CF₃ H H C(O)Pr-c 3,5-(CF₃)₂ CF₃ CH₃ H C(O)Pr-c 3,5-(CF₃)₂ CF₃ CH₃(S) H C(O)Pr-c 3,5-(CF₃)₂ CF₃ CN H C(O)Pr-c 3,5-(CF₃)₂ CF₃ C(S)NH₂ H C(O)Pr-c 3,5-(CF₃)₂ CF₃ H Et C(O)Pr-c 3,5-(CF₃)₂ CF₃ CH₃ Et C(O)Pr-c 3,5-(CF₃)₂ CF₃ CH₃(S) Et C(O)Pr-c 3,5-(CF₃)₂ CF₃ H CH₂Pr-c C(O)Pr-c 3,5-(CF₃)₂ CF₃ CH₃ CH₂Pr-c C(O)Pr-c 3,5-(CF₃)₂ CF₃ H CH₂OCH₃ C(O)Pr-c 3,5-(CF₃)₂ CF₃ CH₃ CH₂CN C(O)Pr-c 3,5-(CF₃)₂ CF₃ CH₃(S) CH₂CN C(O)Pr-c 3,5-(CF₃)₂ CF₃ H CH₂C≡CH C(O)Pr-c 3,5-(CF₃)₂ CF₃ CH₃ CH₂C≡CH C(O)Pr-c 3,5-(CF₃)₂ CF₃ CH₃(S) CH₂C≡CH C(O)Pr-c 3,5-(CF₃)₂ CF₃ H H C(O)Bu-i 3,5-(CF₃)₂ CF₃ CH₃ H C(O)Bu-i 3,5-(CF₃)₂ CF₃ CH₃(S) H C(O)Bu-i 3,5-(CF₃)₂ CF₃ H H C(O)CH₂Pr-c 3,5-(CF₃)₂ CF₃ CH₃ H C(O)CH₂Pr-c 3,5-(CF₃)₂ CF₃ CH₃(S) H C(O)CH₂Pr-c 3,5-(CF₃)₂ CF₃ CN H C(O)CH₂Pr-c 3,5-(CF₃)₂ CF₃ CN(S) H C(O)CH₂Pr-c 3,5-(CF₃)₂ CF₃ H CH₃ C(O)CH₂Pr-c 3,5-(CF₃)₂ CF₃ H Et C(O)CH₂Pr-c 3,5-(CF₃)₂ CF₃ H H C(O)(T-1) 3,5-(CF₃)₂ CF₃ H H C(O)Bu-c 3,5-(CF₃)₂ CF₃ H H C(O)CF₃ 3,5-(CF₃)₂ CF₃ H H C(O)CH₂CH₂Cl 3,5-(CF₃)₂ CF₃ H H C(O)CH₂CF₃ 3,5-(CF₃)₂ CF₃ CH₃ H C(O)CH₂CF₃ 3,5-(CF₃)₂ CF₃ CH₃(S) H C(O)CH₂CF₃ 3,5-(CF₃)₂ CF₃ CN H C(O)CH₂CF₃ 3,5-(CF₃)₂ CF₃ H H C(O)CH₂CH₂CF₃ 3,5-(CF₃)₂ CF₃ H H C(O)(E4-2a) 3,5-(CF₃)₂ CF₃ CH₃ H C(O)(E4-2a) 3,5-(CF₃)₂ CF₃ CH₃(S) H C(O)(E4-2a) 3,5-(CF₃)₂ CF₃ H CH₃ C(O)(E4-2a) 3,5-(CF₃)₂ CF₃ H H C(O)CH₂SCH₃ 3,5-(CF₃)₂ CF₃ CH₃ H C(O)CH₂SCH₃ 3,5-(CF₃)₂ CF₃ H CH₃ C(O)CH₂SCH₃ 3,5-(CF₃)₂ CF₃ H CH₂C≡CH C(O)CH₂SCH₃ 3,5-(CF₃)₂ CF₃ H H C(O)CH₂S(O)CH₃ 3,5-(CF₃)₂ CF₃ CH₃ H C(O)CH₂S(O)CH₃ 3,5-(CF₃)₂ CF₃ H CH₃ C(O)CH₂S(O)CH₃ 3,5-(CF₃)₂ CF₃ H CH₂C≡CH C(O)CH₂S(O)CH₃ 3,5-(CF₃)₂ CF₃ H H C(O)CH₂SO₂CH₃ 3,5-(CF₃)₂ CF₃ CH₃ H C(O)CH₂SO₂CH₃ 3,5-(CF₃)₂ CF₃ H CH₃ C(O)CH₂SO₂CH₃ 3,5-(CF₃)₂ CF₃ H Et C(O)CH₂SO₂CH₃ 3,5-(CF₃)₂ CF₃ H CH₂C≡CH C(O)CH₂SO₂CH₃ 3,5-(CF₃)₂ CF₃ H H C(O)CH₂SEt 3,5-(CF₃)₂ CF₃ CH₃ H C(O)CH₂SEt 3,5-(CF₃)₂ CF₃ H CH₃ C(O)CH₂SEt 3,5-(CF₃)₂ CF₃ H Et C(O)CH₂SEt 3,5-(CF₃)₂ CF₃ H H C(O)CH₂S(O)Et 3,5-(CF₃)₂ CF₃ CH₃ H C(O)CH₂S(O)Et 3,5-(CF₃)₂ CF₃ H H C(O)CH₂SO₂Et 3,5-(CF₃)₂ CF₃ CH₃ H C(O)CH₂SO₂Et 3,5-(CF₃)₂ CF₃ H CH₃ C(O)CH₂SO₂Et 3,5-(CF₃)₂ CF₃ H Et C(O)CH₂SO₂Et 3,5-(CF₃)₂ CF₃ H CH₂C≡CH C(O)CH₂SO₂Et 3,5-(CF₃)₂ CF₃ H H C(O)CH₂SCH₂CF₃ 3,5-(CF₃)₂ CF₃ H H C(O)CH₂SCH₂CN 3,5-(CF₃)₂ CF₃ H H C(O)CH(CH₃)SCH₃ 3,5-(CF₃)₂ CF₃ H H C(O)CH(CH₃)S(O)CH₃ 3,5-(CF₃)₂ CF₃ H H C(O)CH(CH₃)SO₂CH₃ 3,5-(CF₃)₂ CF₃ H H C(O)CH(CH₃)SEt 3,5-(CF₃)₂ CF₃ H H C(O)CH(CH₃)S(O)Et 3,5-(CF₃)₂ CF₃ H H C(O)CH(CH₃)SO₂Et 3,5-(CF₃)₂ CF₃ H H C(O)(E5-1a) 3,5-(CF₃)₂ CF₃ H H C(O)(E5-1b) 3,5-(CF₃)₂ CF₃ H H C(O)(E5-1c) 3,5-(CF₃)₂ CF₃ H H C(O)(E5-2a) 3,5-(CF₃)₂ CF₃ H H C(O)(E5-2b) 3,5-(CF₃)₂ CF₃ H H C(O)(E5-2c) 3,5-(CF₃)₂ CF₃ H H C(O)CF₂SCH₃ 3,5-(CF₃)₂ CF₃ H H C(O)CF₂S(O)CH₃ 3,5-(CF₃)₂ CF₃ H H C(O)CF₂SO₂CH₃ 3,5-(CF₃)₂ CF₃ H H C(O)CH(SCH₃)₂ 3,5-(CF₃)₂ CF₃ H H C(O)CH(SEt)S(O)Et 3,5-(CF₃)₂ CF₃ H H C(O)CH[S(O)Et]₂ 3,5-(CF₃)₂ CF₃ H H C(O)CH[S(O)Et]SO₂Et 3,5-(CF₃)₂ CF₃ H H C(O)CH₂NHCH₂CN 3,5-(CF₃)₂ CF₃ H H C(O)CH₂C(O)NHCH₃ 3,5-(CF₃)₂ CF₃ H H C(O)CH═CH₂ 3,5-(CF₃)₂ CF₃ H H C(O)CH₂CH₂C≡CH 3,5-(CF₃)₂ CF₃ H H C(O)(Ph-2,4,6-F₃) 3,5-(CF₃)₂ CF₃ CH₃ H C(O)(Ph-2,4,6-F₃) 3,5-(CF₃)₂ CF₃ H H C(O)NHEt 3,5-(CF₃)₂ CF₃ CH₃ H C(O)NHEt 3,5-(CF₃)₂ CF₃ CH₃(S) H C(O)NHEt 3,5-(CF₃)₂ CF₃ H H C(O)N(Et)₂ 3,5-(CF₃)₂ CF₃ H H C(O)NHPr-c 3,5-(CF₃)₂ CF₃ CH₃ H C(O)NHPr-c 3,5-(CF₃)₂ CF₃ CH₃(S) H C(O)NHPr-c 3,5-(CF₃)₂ CF₃ H H C(O)NHCH₂CF₃ 3,5-(CF₃)₂ CF₃ CH₃ H C(O)NHCH₂CF₃ 3,5-(CF₃)₂ CF₃ H H C(O)NHCH₂C≡CH 3,5-(CF₃)₂ CF₃ CH₃ H C(O)NHCH₂C≡CH 3,5-(CF₃)₂ CF₃ CH₃(S) H C(O)NHCH₂C≡CH 3,5-(CF₃)₂ CF₃ H H C(S)CH₂SCH₃ 3,5-(CF₃)₂ CF₃ H H C(S)CH₂SEt 3,5-(CF₃)₂ CF₂Cl H H C(O)Et 3,5-(CF₃)₂ CF₂Cl H H C(O)Pr-n 3,5-(CF₃)₂ CF₂Cl H H C(O)Pr-i 3,5-(CF₃)₂ CF₂Cl H H C(O)Pr-c 3,5-(CF₃)₂ CF₂Cl CH₃ H C(O)Pr-c 3,5-(CF₃)₂ CF₂Cl H H C(O)Bu-i 3,5-(CF₃)₂ CF₂Cl H H C(O)CH₂Pr-c 3,5-(CF₃)₂ CF₂Cl CH₃ H C(O)CH₂Pr-c 3,5-(CF₃)₂ CF₂Cl H H C(O)CH₂CF₃ 3,5-(CF₃)₂ CF₂Cl CH₃ H C(O)CH₂CF₃ 3,5-(CF₃)₂ CF₂Cl CH₃ H C(O)(E4-2a) 3,5-(CF₃)₂ CF₂Cl H H C(O)CH₂SCH₃ 3,5-(CF₃)₂ CF₂Cl H H C(O)CH₂S(O)CH₃ 3,5-(CF₃)₂ CF₂Cl H H C(O)CH₂SO₂CH₃ 3,5-(CF₃)₂ CF₂Cl H H C(O)CH₂SEt 3,5-(CF₃)₂ CF₂Cl H H C(O)CH₂S(O)Et 3,5-(CF₃)₂ CF₂Cl H H C(O)CH₂SO₂Et 3,5-(CF₃)₂ CF₂Cl H H C(O)NHEt 3,5-(CF₃)₂ CF₂Cl H H C(O)NHPr-c 3,5-(CF₃)₂ CF₂Cl CH₃ H C(O)NHPr-c 3-Cl-5-OCHF₂ CF₃ H H C(O)Et 3-Cl-5-OCHF₂ CF₃ H H C(O)Pr-n 3-Cl-5-OCHF₂ CF₃ H H C(O)Pr-i 3-Cl-5-OCHF₂ CF₃ H H C(O)Pr-c 3-Cl-5-OCHF₂ CF₃ CH₃ H C(O)Pr-c 3-Cl-5-OCHF₂ CF₃ H H C(O)Bu-i 3-Cl-5-OCHF₂ CF₃ H H C(O)CH₂Pr-c 3-Cl-5-OCHF₂ CF₃ CH₃ H C(O)CH₂Pr-c 3-Cl-5-OCHF₂ CF₃ H H C(O)CH₂CF₃ 3-Cl-5-OCHF₂ CF₃ CH₃ H C(O)CH₂CF₃ 3-Cl-5-OCHF₂ CF₃ CH₃ H C(O)(E4-2a) 3-Cl-5-OCHF₂ CF₃ H H C(O)CH₂SCH₃ 3-Cl-5-OCHF₂ CF₃ H H C(O)CH₂S(O)CH₃ 3-Cl-5-OCHF₂ CF₃ H H C(O)CH₂SO₂CH₃ 3-Cl-5-OCHF₂ CF₃ H H C(O)CH₂SEt 3-Cl-5-OCHF₂ CF₃ H H C(O)CH₂S(O)Et 3-Cl-5-OCHF₂ CF₃ H H C(O)CH₂SO₂Et 3-Cl-5-OCHF₂ CF₃ H H C(O)NHEt 3-Cl-5-OCHF₂ CF₃ H H C(O)NHPr-c 3-Cl-5-OCHF₂ CF₃ CH₃ H C(O)NHPr-c 3-Br-5-OCHF₂ CF₃ H H C(O)Pr-c 3-Br-5-OCHF₂ CF₃ H H C(O)CH₂Pr-c 3-Br-5-OCHF₂ CF₃ H H C(O)CH₂CF₃ 3-Br-5-OCHF₂ CF₃ CH₃ H C(O)(E4-2a) 3-Br-5-OCHF₂ CF₃ H H C(O)CH₂SCH₃ 3-Br-5-OCHF₂ CF₃ H H C(O)CH₂S(O)CH₃ 3-Br-5-OCHF₂ CF₃ H H C(O)CH₂SO₂CH₃ 3-Br-5-OCHF₂ CF₃ H H C(O)CH₂SEt 3-Br-5-OCHF₂ CF₃ H H C(O)CH₂S(O)Et 3-Br-5-OCHF₂ CF₃ H H C(O)CH₂SO₂Et 3-CF₃-5-OCHF₂ CF₃ H H C(O)Pr-c 3-CF₃-5-OCHF₂ CF₃ H H C(O)CH₂Pr-c 3-CF₃-5-OCHF₂ CF₃ H H C(O)CH₂CF₃ 3-CF₃-5-OCHF₂ CF₃ CH₃ H C(O)(E4-2a) 3-CF₃-5-OCHF₂ CF₃ H H C(O)CH₂SCH₃ 3-CF₃-5-OCHF₂ CF₃ H H C(O)CH₂S(O)CH₃ 3-CF₃-5-OCHF₂ CF₃ H H C(O)CH₂SO₂CH₃ 3-CF₃-5-OCHF₂ CF₃ H H C(O)CH₂SEt 3-CF₃-5-OCHF₂ CF₃ H H C(O)CH₂S(O)Et 3-CF₃-5-OCHF₂ CF₃ H H C(O)CH₂SO₂Et 3-Cl-5-OCF₃ CF₃ H H C(O)Et 3-Cl-5-OCF₃ CF₃ H H C(O)Pr-n 3-Cl-5-OCF₃ CF₃ H H C(O)Pr-i 3-Cl-5-OCF₃ CF₃ H H C(O)Pr-c 3-Cl-5-OCF₃ CF₃ CH₃ H C(O)Pr-c 3-Cl-5-OCF₃ CF₃ H H C(O)Bu-i 3-Cl-5-OCF₃ CF₃ H H C(O)CH₂Pr-c 3-Cl-5-OCF₃ CF₃ CH₃ H C(O)CH₂Pr-c 3-Cl-5-OCF₃ CF₃ H H C(O)CH₂CF₃ 3-Cl-5-OCF₃ CF₃ CH₃ H C(O)CH₂CF₃ 3-Cl-5-OCF₃ CF₃ CH₃ H C(O)(E4-2a) 3-Cl-5-OCF₃ CF₃ H H C(O)CH₂SCH₃ 3-Cl-5-OCF₃ CF₃ H H C(O)CH₂S(O)CH₃ 3-Cl-5-OCF₃ CF₃ H H C(O)CH₂SO₂CH₃ 3-Cl-5-OCF₃ CF₃ H H C(O)CH₂SEt 3-Cl-5-OCF₃ CF₃ H H C(O)CH₂S(O)Et 3-Cl-5-OCF₃ CF₃ H H C(O)CH₂SO₂Et 3-Cl-5-OCF₃ CF₃ H H C(O)NHEt 3-Cl-5-OCF₃ CF₃ H H C(O)NHPr-c 3-Cl-5-OCF₃ CF₃ CH₃ H C(O)NHPr-c 3-Br-5-OCF₃ CF₃ H H C(O)Pr-c 3-Br-5-OCF₃ CF₃ H H C(O)CH₂Pr-c 3-Br-5-OCF₃ CF₃ H H C(O)CH₂CF₃ 3-Br-5-OCF₃ CF₃ CH₃ H C(O)(E4-2a) 3-Br-5-OCF₃ CF₃ H H C(O)CH₂SCH₃ 3-Br-5-OCF₃ CF₃ H H C(O)CH₂S(O)CH₃ 3-Br-5-OCF₃ CF₃ H H C(O)CH₂SO₂CH₃ 3-Br-5-OCF₃ CF₃ H H C(O)CH₂SEt 3-Br-5-OCF₃ CF₃ H H C(O)CH₂S(O)Et 3-Br-5-OCF₃ CF₃ H H C(O)CH₂SO₂Et 3-CF₃-5-OCF₃ CF₃ H H C(O)Pr-c 3-CF₃-5-OCF₃ CF₃ H H C(O)CH₂Pr-c 3-CF₃-5-OCF₃ CF₃ H H C(O)CH₂CF₃ 3-CF₃-5-OCF₃ CF₃ CH₃ H C(O)(E4-2a) 3-CF₃-5-OCF₃ CF₃ H H C(O)CH₂SCH₃ 3-CF₃-5-OCF₃ CF₃ H H C(O)CH₂S(O)CH₃ 3-CF₃-5-OCF₃ CF₃ H H C(O)CH₂SO₂CH₃ 3-CF₃-5-OCF₃ CF₃ H H C(O)CH₂SEt 3-CF₃-5-OCF₃ CF₃ H H C(O)CH₂S(O)Et 3-CF₃-5-OCF₃ CF₃ H H C(O)CH₂SO₂Et 3-Cl-5-SCF₃ CF₃ H H C(O)Et 3-Cl-5-SCF₃ CF₃ H H C(O)Pr-n 3-Cl-5-SCF₃ CF₃ H H C(O)Pr-i 3-Cl-5-SCF₃ CF₃ H H C(O)Pr-c 3-Cl-5-SCF₃ CF₃ CH₃ H C(O)Pr-c 3-Cl-5-SCF₃ CF₃ H H C(O)Bu-i 3-Cl-5-SCF₃ CF₃ H H C(O)CH₂Pr-c 3-Cl-5-SCF₃ CF₃ CH₃ H C(O)CH₂Pr-c 3-Cl-5-SCF₃ CF₃ H H C(O)CH₂CF₃ 3-Cl-5-SCF₃ CF₃ CH₃ H C(O)CH₂CF₃ 3-Cl-5-SCF₃ CF₃ CH₃ H C(O)(E4-2a) 3-Cl-5-SCF₃ CF₃ H H C(O)CH₂SCH₃ 3-Cl-5-SCF₃ CF₃ H H C(O)CH₂S(O)CH₃ 3-Cl-5-SCF₃ CF₃ H H C(O)CH₂SO₂CH₃ 3-Cl-5-SCF₃ CF₃ H H C(O)CH₂SEt 3-Cl-5-SCF₃ CF₃ H H C(O)CH₂S(O)Et 3-Cl-5-SCF₃ CF₃ H H C(O)CH₂SO₂Et 3-Cl-5-SCF₃ CF₃ H H C(O)NHEt 3-Cl-5-SCF₃ CF₃ H H C(O)NHPr-c 3-Cl-5-SCF₃ CF₃ CH₃ H C(O)NHPr-c 3-Br-5-SCF₃ CF₃ H H C(O)Pr-c 3-Br-5-SCF₃ CF₃ H H C(O)CH₂Pr-c 3-Br-5-SCF₃ CF₃ H H C(O)CH₂CF₃ 3-Br-5-SCF₃ CF₃ CH₃ H C(O)(E4-2a) 3-Br-5-SCF₃ CF₃ H H C(O)CH₂SCH₃ 3-Br-5-SCF₃ CF₃ H H C(O)CH₂S(O)CH₃ 3-Br-5-SCF₃ CF₃ H H C(O)CH₂SO₂CH₃ 3-Br-5-SCF₃ CF₃ H H C(O)CH₂SEt 3-Br-5-SCF₃ CF₃ H H C(O)CH₂S(O)Et 3-Br-5-SCF₃ CF₃ H H C(O)CH₂SO₂Et 3-CF₃-5-CN CF₃ H H C(O)Pr-c 3-CF₃-5-CN CF₃ H H C(O)CH₂Pr-c 3-CF₃-5-CN CF₃ H H C(O)CH₂CF₃ 3-CF₃-5-CN CF₃ CH₃ H C(O)(E4-2a) 3-CF₃-5-CN CF₃ H H C(O)CH₂SCH₃ 3-CF₃-5-CN CF₃ H H C(O)CH₂S(O)CH₃ 3-CF₃-5-CN CF₃ H H C(O)CH₂SO₂CH₃ 3-CF₃-5-CN CF₃ H H C(O)CH₂SEt 3-CF₃-5-CN CF₃ H H C(O)CH₂S(O)Et 3-CF₃-5-CN CF₃ H H C(O)CH₂SO₂Et 3,4,5-F₃ CF₃ H H C(O)Pr-c 3,4,5-F₃ CF₃ H H C(O)CH₂Pr-c 3,4,5-F₃ CF₃ H H C(O)CH₂CF₃ 3,4,5-F₃ CF₃ CH₃ H C(O)(E4-2a) 3,4,5-F₃ CF₃ H H C(O)CH₂SCH₃ 3,4,5-F₃ CF₃ H H C(O)CH₂S(O)CH₃ 3,4,5-F₃ CF₃ H H C(O)CH₂SO₂CH₃ 3,4,5-F₃ CF₃ H H C(O)CH₂SEt 3,4,5-F₃ CF₃ H H C(O)CH₂S(O)Et 3,4,5-F₃ CF₃ H H C(O)CH₂SO₂Et 3,5-Cl₂-4-F CF₃ H H C(O)CH₃ 3,5-Cl₂-4-F CF₃ H H C(O)Et 3,5-Cl₂-4-F CF₃ CH₃ H C(O)Et 3,5-Cl₂-4-F CF₃ H Et C(O)Et 3,5-Cl₂-4-F CF₃ H CH₂C≡CH C(O)Et 3,5-Cl₂-4-F CF₃ H H C(O)Pr-n 3,5-Cl₂-4-F CF₃ CH₃ H C(O)Pr-n 3,5-Cl₂-4-F CF₃ H Et C(O)Pr-n 3,5-Cl₂-4-F CF₃ H H C(O)Pr-i 3,5-Cl₂-4-F CF₃ CH₃ H C(O)Pr-i 3,5-Cl₂-4-F CF₃ H H C(O)Pr-c 3,5-Cl₂-4-F CF₃ CH₃ H C(O)Pr-c 3,5-Cl₂-4-F CF₃ H Et C(O)Pr-c 3,5-Cl₂-4-F CF₃ CH₃ Et C(O)Pr-c 3,5-Cl₂-4-F CF₃ H CH₂Pr-c C(O)Pr-c 3,5-Cl₂-4-F CF₃ H CH₂OCH₃ C(O)Pr-c 3,5-Cl₂-4-F CF₃ CH₃ CH₂CN C(O)Pr-c 3,5-Cl₂-4-F CF₃ H CH₂C≡CH C(O)Pr-c 3,5-Cl₂-4-F CF₃ CH₃ CH₂C≡CH C(O)Pr-c 3,5-Cl₂-4-F CF₃ H H C(O)Bu-i 3,5-Cl₂-4-F CF₃ CH₃ H C(O)Bu-i 3,5-Cl₂-4-F CF₃ H H C(O)CH₂Pr-c 3,5-Cl₂-4-F CF₃ CH₃ H C(O)CH₂Pr-c 3,5-Cl₂-4-F CF₃ CN H C(O)CH₂Pr-c 3,5-Cl₂-4-F CF₃ H Et C(O)CH₂Pr-c 3,5-Cl₂-4-F CF₃ H H C(O)CH₂CF₃ 3,5-Cl₂-4-F CF₃ CH₃ H C(O)CH₂CF₃ 3,5-Cl₂-4-F CF₃ H H C(O)(E4-2a) 3,5-Cl₂-4-F CF₃ CH₃ H C(O)(E4-2a) 3,5-Cl₂-4-F CF₃ H H C(O)CH₂SCH₃ 3,5-Cl₂-4-F CF₃ H H C(O)CH₂S(O)CH₃ 3,5-Cl₂-4-F CF₃ H H C(O)CH₂SO₂CH₃ 3,5-Cl₂-4-F CF₃ H H C(O)CH₂SEt 3,5-Cl₂-4-F CF₃ H Et C(O)CH₂SEt 3,5-Cl₂-4-F CF₃ H H C(O)CH₂S(O)Et 3,5-Cl₂-4-F CF₃ H H C(O)CH₂SO₂Et 3,5-Cl₂-4-F CF₃ H CH₃ C(O)CH₂SO₂Et 3,5-Cl₂-4-F CF₃ H H C(O)NHEt 3,5-Cl₂-4-F CF₃ CH₃ H C(O)NHEt 3,5-Cl₂-4-F CF₃ H H C(O)NHPr-c 3,5-Cl₂-4-F CF₃ CH₃ H C(O)NHPr-c 3,5-Cl₂-4-F CF₃ CH₃ H C(O)NHCH₂C≡CH 3,5-Cl₂-4-F CF₂Cl H H C(O)Pr-c 3,5-Cl₂-4-F CF₂Cl H H C(O)CH₂Pr-c 3,5-Cl₂-4-F CF₂Cl H H C(O)CH₂CF₃ 3,5-Cl₂-4-F CF₂Cl CH₃ H C(O)(E4-2a) 3,5-Cl₂-4-F CF₂Cl H H C(O)CH₂SCH₃ 3,5-Cl₂-4-F CF₂Cl H H C(O)CH₂S(O)CH₃ 3,5-Cl₂-4-F CF₂Cl H H C(O)CH₂SO₂CH₃ 3,5-Cl₂-4-F CF₂Cl H H C(O)CH₂SEt 3,5-Cl₂-4-F CF₂Cl H H C(O)CH₂S(O)Et 3,5-Cl₂-4-F CF₂Cl H H C(O)CH₂SO₂Et 3,4,5-Cl₃ CF₃ H H C(O)CH₃ 3,4,5-Cl₃ CF₃ H H C(O)Et 3,4,5-Cl₃ CF₃ CH₃ H C(O)Et 3,4,5-Cl₃ CF₃ H Et C(O)Et 3,4,5-Cl₃ CF₃ H CH₂C≡CH C(O)Et 3,4,5-Cl₃ CF₃ H H C(O)Pr-n 3,4,5-Cl₃ CF₃ CH₃ H C(O)Pr-n 3,4,5-Cl₃ CF₃ H Et C(O)Pr-n 3,4,5-Cl₃ CF₃ H H C(O)Pr-i 3,4,5-Cl₃ CF₃ CH₃ H C(O)Pr-i 3,4,5-Cl₃ CF₃ H H C(O)Pr-c 3,4,5-Cl₃ CF₃ CH₃ H C(O)Pr-c 3,4,5-Cl₃ CF₃ H Et C(O)Pr-c 3,4,5-Cl₃ CF₃ CH₃ Et C(O)Pr-c 3,4,5-Cl₃ CF₃ H CH₂Pr-c C(O)Pr-c 3,4,5-Cl₃ CF₃ H CH₂OCH₃ C(O)Pr-c 3,4,5-Cl₃ CF₃ CH₃ CH₂CN C(O)Pr-c 3,4,5-Cl₃ CF₃ H CH₂C≡CH C(O)Pr-c 3,4,5-Cl₃ CF₃ CH₃ CH₂C≡CH C(O)Pr-c 3,4,5-Cl₃ CF₃ H H C(O)Bu-i 3,4,5-Cl₃ CF₃ CH₃ H C(O)Bu-i 3,4,5-Cl₃ CF₃ H H C(O)CH₂Pr-c 3,4,5-Cl₃ CF₃ CH₃ H C(O)CH₂Pr-c 3,4,5-Cl₃ CF₃ CN H C(O)CH₂Pr-c 3,4,5-Cl₃ CF₃ H Et C(O)CH₂Pr-c 3,4,5-Cl₃ CF₃ H H C(O)CH₂CF₃ 3,4,5-Cl₃ CF₃ CH₃ H C(O)CH₂CF₃ 3,4,5-Cl₃ CF₃ H H C(O)(E4-2a) 3,4,5-Cl₃ CF₃ CH₃ H C(O)(E4-2a) 3,4,5-Cl₃ CF₃ H H C(O)CH₂SCH₃ 3,4,5-Cl₃ CF₃ H H C(O)CH₂S(O)CH₃ 3,4,5-Cl₃ CF₃ H H C(O)CH₂SO₂CH₃ 3,4,5-Cl₃ CF₃ H H C(O)CH₂SEt 3,4,5-Cl₃ CF₃ H Et C(O)CH₂SEt 3,4,5-Cl₃ CF₃ H H C(O)CH₂S(O)Et 3,4,5-Cl₃ CF₃ H H C(O)CH₂SO₂Et 3,4,5-Cl₃ CF₃ H CH₃ C(O)CH₂SO₂Et 3,4,5-Cl₃ CF₃ H H C(O)NHEt 3,4,5-Cl₃ CF₃ CH₃ H C(O)NHEt 3,4,5-Cl₃ CF₃ H H C(O)NHPr-c 3,4,5-Cl₃ CF₃ CH₃ H C(O)NHPr-c 3,4,5-Cl₃ CF₃ CH₃ H C(O)NHCH₂C≡CH 3,4,5-Cl₃ CF₂Cl H H C(O)Pr-c 3,4,5-Cl₃ CF₂Cl H H C(O)CH₂Pr-c 3,4,5-Cl₃ CF₂Cl H H C(O)CH₂CF₃ 3,4,5-Cl₃ CF₂Cl CH₃ H C(O)(E4-2a) 3,4,5-Cl₃ CF₂Cl H H C(O)CH₂SCH₃ 3,4,5-Cl₃ CF₂Cl H H C(O)CH₂S(O)CH₃ 3,4,5-Cl₃ CF₂Cl H H C(O)CH₂SO₂CH₃ 3,4,5-Cl₃ CF₂Cl H H C(O)CH₂SEt 3,4,5-Cl₃ CF₂Cl H H C(O)CH₂S(O)Et 3,4,5-Cl₃ CF₂Cl H H C(O)CH₂SO₂Et 3,5-Br₂-4-F CF₃ H H C(O)CH₃ 3,5-Br₂-4-F CF₃ H H C(O)Et 3,5-Br₂-4-F CF₃ CH₃ H C(O)Et 3,5-Br₂-4-F CF₃ H Et C(O)Et 3,5-Br₂-4-F CF₃ H CH₂C≡CH C(O)Et 3,5-Br₂-4-F CF₃ H H C(O)Pr-n 3,5-Br₂-4-F CF₃ CH₃ H C(O)Pr-n 3,5-Br₂-4-F CF₃ H Et C(O)Pr-n 3,5-Br₂-4-F CF₃ H H C(O)Pr-i 3,5-Br₂-4-F CF₃ CH₃ H C(O)Pr-i 3,5-Br₂-4-F CF₃ H H C(O)Pr-c 3,5-Br₂-4-F CF₃ CH₃ H C(O)Pr-c 3,5-Br₂-4-F CF₃ H Et C(O)Pr-c 3,5-Br₂-4-F CF₃ CH₃ Et C(O)Pr-c 3,5-Br₂-4-F CF₃ H CH₂Pr-c C(O)Pr-c 3,5-Br₂-4-F CF₃ H CH₂OCH₃ C(O)Pr-c 3,5-Br₂-4-F CF₃ CH₃ CH₂CN C(O)Pr-c 3,5-Br₂-4-F CF₃ H CH₂C≡CH C(O)Pr-c 3,5-Br₂-4-F CF₃ CH₃ CH₂C≡CH C(O)Pr-c 3,5-Br₂-4-F CF₃ H H C(O)Bu-i 3,5-Br₂-4-F CF₃ CH₃ H C(O)Bu-i 3,5-Br₂-4-F CF₃ H H C(O)CH₂Pr-c 3,5-Br₂-4-F CF₃ CH₃ H C(o)CH₂Pr-c 3,5-Br₂-4-F CF₃ CN H C(O)CH₂Pr-c 3,5-Br₂-4-F CF₃ H Et C(O)CH₂Pr-c 3,5-Br₂-4-F CF₃ H H C(O)CH₂CF₃ 3,5-Br₂-4-F CF₃ CH₃ H C(O)CH₂CF₃ 3,5-Br₂-4-F CF₃ H H C(O)(E4-2a) 3,5-Br₂-4-F CF₃ CH₃ H C(O)(E4-2a) 3,5-Br₂-4-F CF₃ H H C(O)CH₂SCH₃ 3,5-Br₂-4-F CF₃ H H C(O)CH₂S(O)CH₃ 3,5-Br₂-4-F CF₃ H H C(O)CH₂SO₂CH₃ 3,5-Br₂-4-F CF₃ H H C(O)CH₂SEt 3,5-Br₂-4-F CF₃ H Et C(O)CH₂SEt 3,5-Br₂-4-F CF₃ H H C(O)CH₂S(O)Et 3,5-Br₂-4-F CF₃ H H C(O)CH₂SO₂Et 3,5-Br₂-4-F CF₃ H CH₃ C(O)CH₂SO₂Et 3,5-Br₂-4-F CF₃ H H C(O)NHEt 3,5-Br₂-4-F CF₃ CH₃ H C(O)NHEt 3,5-Br₂-4-F CF₃ H H C(O)NHPr-c 3,5-Br₂-4-F CF₃ CH₃ H C(O)NHPr-c 3,5-Br₂-4-F CF₃ CH₃ H C(O)NHCH₂C≡CH 3,5-Br₂-4-F CF₂Cl H H C(O)Pr-c 3,5-Br₂-4-F CF₂Cl H H C(O)CH₂Pr-c 3,5-Br₂-4-F CF₂Cl H H C(O)CH₂CF₃ 3,5-Br₂-4-F CF₂Cl CH₃ H C(O)(E4-2a) 3,5-Br₂-4-F CF₂Cl H H C(O)CH₂SCH₃ 3,5-Br₂-4-F CF₂Cl H H C(O)CH₂S(O)CH₃ 3,5-Br₂-4-F CF₂Cl H H C(O)CH₂SO₂CH₃ 3,5-Br₂-4-F CF₂Cl H H C(O)CH₂SEt 3,5-Br₂-4-F CF₂Cl H H C(O)CH₂S(O)Et 3,5-Br₂-4-F CF₂Cl H H C(O)CH₂SO₂Et 3,4,5-Br₃ CF₃ H H C(O)Pr-c 3,4,5-Br₃ CF₃ H H C(O)CH₂Pr-c 3,4,5-Br₃ CF₃ H H C(O)CH₂CF₃ 3,4,5-Br₃ CF₃ CH₃ H C(O)(E4-2a) 3,4,5-Br₃ CF₃ H H C(O)CH₂SCH₃ 3,4,5-Br₃ CF₃ H H C(O)CH₂S(O)CH₃ 3,4,5-Br₃ CF₃ H H C(O)CH₂SO₂CH₃ 3,4,5-Br₃ CF₃ H H C(O)CH₂SEt 3,4,5-Br₃ CF₃ H H C(O)CH₂S(O)Et 3,4,5-Br₃ CF₃ H H C(O)CH₂SO₂Et 3,4-F₂-5-CF₃ CF₃ H H C(O)CH₃ 3,4-F₂-5-CF₃ CF₃ H H C(O)Et 3,4-F₂-5-CF₃ CF₃ CH₃ H C(O)Et 3,4-F₂-5-CF₃ CF₃ H Et C(O)Et 3,4-F₂-5-CF₃ CF₃ H CH₂C≡CH C(O)Et 3,4-F₂-5-CF₃ CF₃ H H C(O)Pr-n 3,4-F₂-5-CF₃ CF₃ CH₃ H C(O)Pr-n 3,4-F₂-5-CF₃ CF₃ H Et C(O)Pr-n 3,4-F₂-5-CF₃ CF₃ H H C(O)Pr-i 3,4-F₂-5-CF₃ CF₃ CH₃ H C(O)Pr-i 3,4-F₂-5-CF₃ CF₃ H H C(O)Pr-c 3,4-F₂-5-CF₃ CF₃ CH₃ H C(O)Pr-c 3,4-F₂-5-CF₃ CF₃ H Et C(O)Pr-c 3,4-F₂-5-CF₃ CF₃ CH₃ Et C(O)Pr-c 3,4-F₂-5-CF₃ CF₃ H CH₂Pr-c C(O)Pr-c 3,4-F₂-5-CF₃ CF₃ H CH₂OCH₃ C(O)Pr-c 3,4-F₂-5-CF₃ CF₃ CH₃ CH₂CN C(O)Pr-c 3,4-F₂-5-CF₃ CF₃ H CH₂C≡CH C(O)Pr-c 3,4-F₂-5-CF₃ CF₃ CH₃ CH₂C≡CH C(O)Pr-c 3,4-F₂-5-CF₃ CF₃ H H C(O)Bu-i 3,4-F₂-5-CF₃ CF₃ CH₃ H C(O)Bu-i 3,4-F₂-5-CF₃ CF₃ H H C(O)CH₂Pr-c 3,4-F₂-5-CF₃ CF₃ CH₃ H C(O)CH₂Pr-c 3,4-F₂-5-CF₃ CF₃ CN H C(O)CH₂Pr-c 3,4-F₂-5-CF₃ CF₃ H Et C(O)CH₂Pr-c 3,4-F₂-5-CF₃ CF₃ H H C(O)CH₂CF₃ 3,4-F₂-5-CF₃ CF₃ CH₃ H C(O)CH₂CF₃ 3,4-F₂-5-CF₃ CF₃ H H C(O)(E4-2a) 3,4-F₂-5-CF₃ CF₃ CH₃ H C(O)(E4-2a) 3,4-F₂-5-CF₃ CF₃ H H C(O)CH₂SCH₃ 3,4-F₂-5-CF₃ CF₃ H H C(O)CH₂S(O)CH₃ 3,4-F₂-5-CF₃ CF₃ H H C(O)CH₂SO₂CH₃ 3,4-F₂-5-CF₃ CF₃ H H C(O)CH₂SEt 3,4-F₂-5-CF₃ CF₃ H Et C(O)CH₂SEt 3,4-F₂-5-CF₃ CF₃ H H C(O)CH₂S(O)Et 3,4-F₂-5-CF₃ CF₃ H H C(O)CH₂SO₂Et 3,4-F₂-5-CF₃ CF₃ H CH₃ C(O)CH₂SO₂Et 3,4-F₂-5-CF₃ CF₃ H H C(O)NHEt 3,4-F₂-5-CF₃ CF₃ CH₃ H C(O)NHEt 3,4-F₂-5-CF₃ CF₃ H H C(O)NHPr-c 3,4-F₂-5-CF₃ CF₃ CH₃ H C(O)NHPr-c 3,4-F₂-5-CF₃ CF₃ CH₃ H C(O)NHCH₂C≡CH 3,4-F₂-5-CF₃ CF₂Cl H H C(O)Pr-c 3,4-F₂-5-CF₃ CF₂Cl H H C(O)CH₂Pr-c 3,4-F₂-5-CF₃ CF₂Cl H H C(O)CH₂CF₃ 3,4-F₂-5-CF₃ CF₂Cl CH₃ H C(O)(E4-2a) 3,4-F₂-5-CF₃ CF₂Cl H H C(O)CH₂SCH₃ 3,4-F₂-5-CF₃ CF₂Cl H H C(O)CH₂S(O)CH₃ 3,4-F₂-5-CF₃ CF₂Cl H H C(O)CH₂SO₂CH₃ 3,4-F₂-5-CF₃ CF₂Cl H H C(O)CH₂SEt 3,4-F₂-5-CF₃ CF₂Cl H H C(O)CH₂S(O)Et 3,4-F₂-5-CF₃ CF₂Cl H H C(O)CH₂SO₂Et 3-Cl-4-F-5-CF₃ CF₃ H H C(O)CH₃ 3-Cl-4-F-5-CF₃ CF₃ H H C(O)Et 3-Cl-4-F-5-CF₃ CF₃ CH₃ H C(O)Et 3-Cl-4-F-5-CF₃ CF₃ H Et C(O)Et 3-Cl-4-F-5-CF₃ CF₃ H CH₂C≡CH C(O)Et 3-Cl-4-F-5-CF₃ CF₃ H H C(O)Pr-n 3-Cl-4-F-5-CF₃ CF₃ CH₃ H C(O)Pr-n 3-Cl-4-F-5-CF₃ CF₃ H Et C(O)Pr-n 3-Cl-4-F-5-CF₃ CF₃ H H C(O)Pr-i 3-Cl-4-F-5-CF₃ CF₃ CH₃ H C(O)Pr-i 3-Cl-4-F-5-CF₃ CF₃ H H C(O)Pr-c 3-Cl-4-F-5-CF₃ CF₃ CH₃ H C(O)Pr-c 3-Cl-4-F-5-CF₃ CF₃ H Et C(O)Pr-c 3-Cl-4-F-5-CF₃ CF₃ CH₃ Et C(O)Pr-c 3-Cl-4-F-5-CF₃ CF₃ H CH₂Pr-c C(O)Pr-c 3-Cl-4-F-5-CF₃ CF₃ H CH₂OCH₃ C(O)Pr-c 3-Cl-4-F-5-CF₃ CF₃ CH₃ CH₂CN C(O)Pr-c 3-Cl-4-F-5-CF₃ CF₃ H CH₂C≡CH C(O)Pr-c 3-Cl-4-F-5-CF₃ CF₃ CH₃ CH₂C≡CH C(O)Pr-c 3-Cl-4-F-5-CF₃ CF₃ H H C(O)Bu-i 3-Cl-4-F-5-CF₃ CF₃ CH₃ H C(O)Bu-i 3-Cl-4-F-5-CF₃ CF₃ H H C(O)CH₂Pr-c 3-Cl-4-F-5-CF₃ CF₃ CH₃ H C(O)CH₂Pr-c 3-Cl-4-F-5-CF₃ CF₃ CN H C(O)CH₂Pr-c 3-Cl-4-F-5-CF₃ CF₃ H Et C(O)CH₂Pr-c 3-Cl-4-F-5-CF₃ CF₃ H H C(O)CH₂CF₃ 3-Cl-4-F-5-CF₃ CF₃ CH₃ H C(O)CH₂CF₃ 3-Cl-4-F-5-CF₃ CF₃ H H C(O)(E4-2a) 3-Cl-4-F-5-CF₃ CF₃ CH₃ H C(O)(E4-2a) 3-Cl-4-F-5-CF₃ CF₃ H H C(O)CH₂SCH₃ 3-Cl-4-F-5-CF₃ CF₃ H H C(O)CH₂S(O)CH₃ 3-Cl-4-F-5-CF₃ CF₃ H H C(O)CH₂SO₂CH₃ 3-Cl-4-F-5-CF₃ CF₃ H H C(O)CH₂SEt 3-Cl-4-F-5-CF₃ CF₃ H Et C(O)CH₂SEt 3-Cl-4-F-5-CF₃ CF₃ H H C(O)CH₂S(O)Et 3-Cl-4-F-5-CF₃ CF₃ H H C(O)CH₂SO₂Et 3-Cl-4-F-5-CF₃ CF₃ H CH₃ C(O)CH₂SO₂Et 3-Cl-4-F-5-CF₃ CF₃ H H C(O)NHEt 3-Cl-4-F-5-CF₃ CF₃ CH₃ H C(O)NHEt 3-Cl-4-F-5-CF₃ CF₃ H H C(O)NHPr-c 3-Cl-4-F-5-CF₃ CF₃ CH₃ H C(O)NHPr-c 3-Cl-4-F-5-CF₃ CF₃ CH₃ H C(O)NHCH₂C≡CH 3-Cl-4-F-5-CF₃ CF₂Cl H H C(O)Pr-c 3-Cl-4-F-5-CF₃ CF₂Cl H H C(O)CH₂Pr-c 3-Cl-4-F-5-CF₃ CF₂Cl H H C(O)CH₂CF₃ 3-Cl-4-F-5-CF₃ CF₂Cl CH₃ H C(O)(E4-2a) 3-Cl-4-F-5-CF₃ CF₂Cl H H C(O)CH₂SCH₃ 3-Cl-4-F-5-CF₃ CF₂Cl H H C(O)CH₂S(O)CH₃ 3-Cl-4-F-5-CF₃ CF₂Cl H H C(O)CH₂SO₂CH₃ 3-Cl-4-F-5-CF₃ CF₂Cl H H C(O)CH₂SEt 3-Cl-4-F-5-CF₃ CF₂Cl H H C(O)CH₂S(O)Et 3-Cl-4-F-5-CF₃ CF₂Cl H H C(O)CH₂SO₂Et 3,4-Cl₂-5-CF₃ CF₃ H H C(O)CH₃ 3,4-Cl₂-5-CF₃ CF₃ H H C(O)Et 3,4-Cl₂-5-CF₃ CF₃ CH₃ H C(O)Et 3,4-Cl₂-5-CF₃ CF₃ H Et C(O)Et 3,4-Cl₂-5-CF₃ CF₃ H CH₂C≡CH C(O)Et 3,4-Cl₂-5-CF₃ CF₃ H H C(O)Pr-n 3,4-Cl₂-5-CF₃ CF₃ CH₃ H C(O)Pr-n 3,4-Cl₂-5-CF₃ CF₃ H Et C(O)Pr-n 3,4-Cl₂-5-CF₃ CF₃ H H C(O)Pr-i 3,4-Cl₂-5-CF₃ CF₃ CH₃ H C(O)Pr-i 3,4-Cl₂-5-CF₃ CF₃ H H C(O)Pr-c 3,4-Cl₂-5-CF₃ CF₃ CH₃ H C(O)Pr-c 3,4-Cl₂-5-CF₃ CF₃ H Et C(O)Pr-c 3,4-Cl₂-5-CF₃ CF₃ CH₃ Et C(O)Pr-c 3,4-Cl₂-5-CF₃ CF₃ H CH₂Pr-c C(O)Pr-c 3,4-Cl₂-5-CF₃ CF₃ H CH₂OCH₃ C(O)Pr-c 3,4-Cl₂-5-CF₃ CF₃ CH₃ CH₂CN C(O)Pr-c 3,4-Cl₂-5-CF₃ CF₃ H CH₂C≡CH C(O)Pr-c 3,4-Cl₂-5-CF₃ CF₃ CH₃ CH₂C≡CH C(O)Pr-c 3,4-Cl₂-5-CF₃ CF₃ H H C(O)Bu-i 3,4-Cl₂-5-CF₃ CF₃ CH₃ H C(O)Bu-i 3,4-Cl₂-5-CF₃ CF₃ H H C(O)CH₂Pr-c 3,4-Cl₂-5-CF₃ CF₃ CH₃ H C(O)CH₂Pr-c 3,4-Cl₂-5-CF₃ CF₃ CN H C(O)CH₂Pr-c 3,4-Cl₂-5-CF₃ CF₃ H Et C(O)CH₂Pr-c 3,4-Cl₂-5-CF₃ CF₃ H H C(O)CH₂CF₃ 3,4-Cl₂-5-CF₃ CF₃ CH₃ H C(O)CH₂CF₃ 3,4-Cl₂-5-CF₃ CF₃ H H C(O)(E4-2a) 3,4-Cl₂-5-CF₃ CF₃ CH₃ H C(O)(E4-2a) 3,4-Cl₂-5-CF₃ CF₃ H H C(O)CH₂SCH₃ 3,4-Cl₂-5-CF₃ CF₃ H H C(O)CH₂S(O)CH₃ 3,4-Cl₂-5-CF₃ CF₃ H H C(O)CH₂SO₂CH₃ 3,4-Cl₂-5-CF₃ CF₃ H H C(O)CH₂SEt 3,4-Cl₂-5-CF₃ CF₃ H Et C(O)CH₂SEt 3,4-Cl₂-5-CF₃ CF₃ H H C(O)CH₂S(O)Et 3,4-Cl₂-5-CF₃ CF₃ H H C(O)CH₂SO₂Et 3,4-Cl₂-5-CF₃ CF₃ H CH₃ C(O)CH₂SO₂Et 3,4-Cl₂-5-CF₃ CF₃ H H C(O)NHEt 3,4-Cl₂-5-CF₃ CF₃ CH₃ H C(O)NHEt 3,4-Cl₂-5-CF₃ CF₃ H H C(O)NHPr-c 3,4-Cl₂-5-CF₃ CF₃ CH₃ H C(O)NHPr-c 3,4-Cl₂-5-CF₃ CF₃ CH₃ H C(O)NHCH₂C≡CH 3,4-Cl₂-5-CF₃ CF₂Cl H H C(O)Pr-c 3,4-Cl₂-5-CF₃ CF₂Cl H H C(O)CH₂Pr-c 3,4-Cl₂-5-CF₃ CF₂Cl H H C(O)CH₂CF₃ 3,4-Cl₂-5-CF₃ CF₂Cl CH₃ H C(O)(E4-2a) 3,4-Cl₂-5-CF₃ CF₂Cl H H C(O)CH₂SCH₃ 3,4-Cl₂-5-CF₃ CF₂Cl H H C(O)CH₂S(O)CH₃ 3,4-Cl₂-5-CF₃ CF₂Cl H H C(O)CH₂SO₂CH₃ 3,4-Cl₂-5-CF₃ CF₂Cl H H C(O)CH₂SEt 3,4-Cl₂-5-CF₃ CF₂Cl H H C(O)CH₂S(O)Et 3,4-Cl₂-5-CF₃ CF₂Cl H H C(O)CH₂SO₂Et 3,5-(CF₃)₂-4-Cl CF₃ H H C(O)CH₃ 3,5-(CF₃)₂-4-Cl CF₃ H H C(O)Et 3,5-(CF₃)₂-4-Cl CF₃ CH₃ H C(O)Et 3,5-(CF₃)₂-4-Cl CF₃ H Et C(O)Et 3,5-(CF₃)₂-4-Cl CF₃ H CH₂C≡CH C(O)Et 3,5-(CF₃)₂-4-Cl CF₃ H H C(O)Pr-n 3,5-(CF₃)₂-4-Cl CF₃ CH₃ H C(O)Pr-n 3,5-(CF₃)₂-4-Cl CF₃ H Et C(O)Pr-n 3,5-(CF₃)₂-4-Cl CF₃ H H C(O)Pr-i 3,5-(CF₃)₂-4-Cl CF₃ CH₃ H C(O)Pr-i 3,5-(CF₃)₂-4-Cl CF₃ H H C(O)Pr-c 3,5-(CF₃)₂-4-Cl CF₃ CH₃ H C(O)Pr-c 3,5-(CF₃)₂-4-Cl CF₃ H Et C(O)Pr-c 3,5-(CF₃)₂-4-Cl CF₃ CH₃ Et C(O)Pr-c 3,5-(CF₃)₂-4-Cl CF₃ H CH₂Pr-c C(O)Pr-c 3,5-(CF₃)₂-4-Cl CF₃ H CH₂OCH₃ C(O)Pr-c 3,5-(CF₃)₂-4-Cl CF₃ CH₃ CH₂CN C(O)Pr-c 3,5-(CF₃)₂-4-Cl CF₃ H CH₂C≡CH C(O)Pr-c 3,5-(CF₃)₂-4-Cl CF₃ CH₃ CH₂C≡CH C(O)Pr-c 3,5-(CF₃)₂-4-Cl CF₃ H H C(O)Bu-i 3,5-(CF₃)₂-4-Cl CF₃ CH₃ H C(O)Bu-i 3,5-(CF₃)₂-4-Cl CF₃ H H C(O)CH₂Pr-c 3,5-(CF₃)₂-4-Cl CF₃ CH₃ H C(O)CH₂Pr-c 3,5-(CF₃)₂-4-Cl CF₃ CN H C(O)CH₂Pr-c 3,5-(CF₃)₂-4-Cl CF₃ H Et C(O)CH₂Pr-c 3,5-(CF₃)₂-4-Cl CF₃ H H C(O)CH₂CF₃ 3,5-(CF₃)₂-4-Cl CF₃ CH₃ H C(O)CH₂CF₃ 3,5-(CF₃)₂-4-Cl CF₃ H H C(O)(E4-2a) 3,5-(CF₃)₂-4-Cl CF₃ CH₃ H C(O)(E4-2a) 3,5-(CF₃)₂-4-Cl CF₃ H H C(O)CH₂SCH₃ 3,5-(CF₃)₂-4-Cl CF₃ H H C(O)CH₂S(O)CH₃ 3,5-(CF₃)₂-4-Cl CF₃ H H C(O)CH₂SO₂CH₃ 3,5-(CF₃)₂-4-Cl CF₃ H H C(O)CH₂SEt 3,5-(CF₃)₂-4-Cl CF₃ H Et C(O)CH₂SEt 3,5-(CF₃)₂-4-Cl CF₃ H H C(O)CH₂S(O)Et 3,5-(CF₃)₂-4-Cl CF₃ H H C(O)CH₂SO₂Et 3,5-(CF₃)₂-4-Cl CF₃ H CH₃ C(O)CH₂SO₂Et 3,5-(CF₃)₂-4-Cl CF₃ H H C(O)NHEt 3,5-(CF₃)₂-4-Cl CF₃ CH₃ H C(O)NHEt 3,5-(CF₃)₂-4-Cl CF₃ H H C(O)NHPr-c 3,5-(CF₃)₂-4-Cl CF₃ CH₃ H C(O)NHPr-c 3,5-(CF₃)₂-4-Cl CF₃ CH₃ H C(O)NHCH₂C≡CH 3,5-(CF₃)₂-4-Cl CF₂Cl H H C(O)Pr-c 3,5-(CF₃)₂-4-Cl CF₂Cl H H C(O)CH₂Pr-c 3,5-(CF₃)₂-4-Cl CF₂Cl H H C(O)CH₂CF₃ 3,5-(CF₃)₂-4-Cl CF₂Cl CH₃ H C(O)(E4-2a) 3,5-(CF₃)₂-4-Cl CF₂Cl H H C(O)CH₂SCH₃ 3,5-(CF₃)₂-4-Cl CF₂Cl H H C(O)CH₂S(O)CH₃ 3,5-(CF₃)₂-4-Cl CF₂Cl H H C(O)CH₂SO₂CH₃ 3,5-(CF₃)₂-4-Cl CF₂Cl H H C(O)CH₂SEt 3,5-(CF₃)₂-4-Cl CF₂Cl H H C(O)CH₂S(O)Et 3,5-(CF₃)₂-4-Cl CF₂Cl H H C(O)CH₂SO₂Et 3,5-Cl₂-4-OCHF₂ CF₃ H H C(O)Pr-c 3,5-Cl₂-4-OCHF₂ CF₃ H H C(O)CH₂Pr-c 3,5-Cl₂-4-OCHF₂ CF₃ H H C(O)CH₂CF₃ 3,5-Cl₂-4-OCHF₂ CF₃ CH₃ H C(O)(E4-2a) 3,5-Cl₂-4-OCHF₂ CF₃ H H C(O)CH₂SCH₃ 3,5-Cl₂-4-OCHF₂ CF₃ H H C(O)CH₂S(O)CH₃ 3,5-Cl₂-4-OCHF₂ CF₃ H H C(O)CH₂SO₂CH₃ 3,5-Cl₂-4-OCHF₂ CF₃ H H C(O)CH₂SEt 3,5-Cl₂-4-OCHF₂ CF₃ H H C(O)CH₂S(O)Et 3,5-Cl₂-4-OCHF₂ CF₃ H H C(O)CH₂SO₂Et 3,5-Br₂-4-OCHF₂ CF₃ H H C(O)Pr-c 3,5-Br₂-4-OCHF₂ CF₃ H H C(O)CH₂Pr-c 3,5-Br₂-4-OCHF₂ CF₃ H H C(O)CH₂CF₃ 3,5-Br₂-4-OCHF₂ CF₃ CH₃ H C(O)(E4-2a) 3,5-Br₂-4-OCHF₂ CF₃ H H C(O)CH₂SCH₃ 3,5-Br₂-4-OCHF₂ CF₃ H H C(O)CH₂S(O)CH₃ 3,5-Br₂-4-OCHF₂ CF₃ H H C(O)CH₂SO₂CH₃ 3,5-Br₂-4-OCHF₂ CF₃ H H C(O)CH₂SEt 3,5-Br₂-4-OCHF₂ CF₃ H H C(O)CH₂S(O)Et 3,5-Br₂-4-OCHF₂ CF₃ H H C(O)CH₂SO₂Et

Compounds represented by Structure Formulae [1]-1 to [1]-110 and [2]-1 to [2]-75 having structures in which G² is represented by G²-4 to G²-11.

In Table, the number representing the substitution site of the substituent (X)_(m) corresponds to the site indicated by the number in each of Structure Formulae [1]-1 to [1]-110 and [2]-1 to [2]-75, the number representing the substitution site of a substituent (Z^(a))_(p) corresponds to the site indicated by the number in G²-4 to G²-11, and the expression of “-” represents unsubstituted.

(X)_(m) R³ G² (Z^(a))_(p) 3-Br CF₃ G²-7 — 3-I CF₃ G²-7 — 3-I CF₃ G²-10 — 3-CF₃ CF₃ G²-7 — 3-CF₃ CF₃ G²-10 — 3-CF₂CF₃ CF₃ G²-7 — 3-OCF₃ CF₃ G²-7 — 3-SCF₃ CF₃ G²-7 — 3-SF₅ CF₃ G²-7 — 3-Cl-4-F CF₃ G²-7 — 3-Cl-4-F CF₃ G²-10 — 3,4-Cl₂ CF₃ G²-7 — 3,4-Cl₂ CF₃ G²-10 — 3,5-Cl₂ CF₃ G²-4 4-C(O)NHCH₂CF₃ 3,5-Cl₂ CF₃ G²-6 — 3,5-Cl₂ CF₃ G²-7 — 3,5-Cl₂ CF₃ G²-9 — 3,5-Cl₂ CF₃ G²-10 — 3,5-Cl₂ CF₃ G²-10 CH₃ 3,5-Cl₂ CF₂Cl G²-7 — 3-Br-4-F CF₃ G²-7 — 3-Br-4-F CF₃ G²-10 — 3-F-5-Br CF₃ G²-7 — 3-F-5-Br CF₃ G²-10 — 3-Br-4-Cl CF₃ G²-7 — 3-Cl-4-Br CF₃ G²-7 — 3-Cl-5-Br CF₃ G²-4 4-C(O)NHCH₂CF₃ 3-Cl-5-Br CF₃ G²-6 — 3-Cl-5-Br CF₃ G²-7 — 3-Cl-5-Br CF₃ G²-9 — 3-Cl-5-Br CF₃ G²-10 — 3-Cl-5-Br CF₃ G²-10 CH₃ 3-Cl-5-Br CF₂Cl G²-7 — 3,4-Br₂ CF₃ G²-7 — 3,5-Br₂ CF₃ G²-4 4-C(O)NHCH₂CF₃ 3,5-Br₂ CF₃ G²-6 — 3,5-Br₂ CF₃ G²-7 — 3,5-Br₂ CF₃ G²-9 — 3,5-Br₂ CF₃ G²-10 — 3,5-Br₂ CF₃ G²-10 CH₃ 3,5-Br₂ CF₂Cl G²-7 — 3-I-4-F CF₃ G²-7 — 3-F-5-I CF₃ G²-7 — 3-Cl-5-I CF₃ G²-7 — 3-Cl-5-I CF₃ G²-10 — 3-CF₃-4-F CF₃ G²-7 — 3-CF₃-4-F CF₃ G²-10 — 3-F-5-CF₃ CF₃ G²-7 — 3-F-5-CF₃ CF₃ G²-10 — 3-CF₃-4-Cl CF₃ G²-7 — 3-CF₃-4-Cl CF₃ G²-10 — 3-Cl-5-CF₃ CF₃ G²-4 4-C(O)NHCH₂CF₃ 3-Cl-5-CF₃ CF₃ G²-6 — 3-Cl-5-CF₃ CF₃ G²-7 — 3-Cl-5-CF₃ CF₃ G²-9 — 3-Cl-5-CF₃ CF₃ G²-10 — 3-Cl-5-CF₃ CF₃ G²-10 CH₃ 3-Cl-5-CF₃ CF₂Cl G²-7 — 3-Br-5-CF₃ CF₃ G²-4 4-C(O)NHCH₂CF₃ 3-Br-5-CF₃ CF₃ G²-6 — 3-Br-5-CF₃ CF₃ G²-7 — 3-Br-5-CF₃ CF₃ G²-9 — 3-Br-5-CF₃ CF₃ G²-10 — 3-Br-5-CF₃ CF₃ G²-10 CH₃ 3-Br-5-CF₃ CF₂Cl G²-7 — 3,5-(CF₃)₂ CF₃ G²-4 — 3,5-(CF₃)₂ CF₃ G²-4 4-F 3,5-(CF₃)₂ CF₃ G²-4 4-Br 3,5-(CF₃)₂ CF₃ G²-4 4-C(O)NHCH₂CF₃ 3,5-(CF₃)₂ CF₃ G²-4 4-NO₂ 3,5-(CF₃)₂ CF₃ G²-5 — 3,5-(CF₃)₂ CF₃ G²-6 — 3,5-(CF₃)₂ CF₃ G²-7 — 3,5-(CF₃)₂ CF₃ G²-7 3-Br 3,5-(CF₃)₂ CF₃ G²-7 5-Br 3,5-(CF₃)₂ CF₃ G²-7 3-NH₂ 3,5-(CF₃)₂ CF₃ G²-7 5-NH₂ 3,5-(CF₃)₂ CF₃ G²-8 — 3,5-(CF₃)₂ CF₃ G²-9 — 3,5-(CF₃)₂ CF₃ G²-10 — 3,5-(CF₃)₂ CF₃ G²-10 CH₃ 3,5-(CF₃)₂ CF₃ G²-11 — 3,5-(CF₃)₂ CF₂Cl G²-7 — 3,5-(CF₃)₂ CF₂Cl G²-10 — 3-Cl-5-OCHF₂ CF₃ G²-7 — 3-Cl-5-OCHF₂ CF₃ G²-10 — 3-Br-5-OCHF₂ CF₃ G²-7 — 3-CF₃-5-OCHF₂ CF₃ G²-7 — 3-Cl-5-OCF₃ CF₃ G²-7 — 3-Cl-5-OCF₃ CF₃ G²-10 — 3-Br-5-OCF₃ CF₃ G²-7 — 3-CF₃-5-OCF₃ CF₃ G²-7 — 3-Cl-5-SCF₃ CF₃ G²-7 — 3-Cl-5-SCF₃ CF₃ G²-10 — 3-Br-5-SCF₃ CF₃ G²-7 — 3-CF₃-5-CN CF₃ G²-7 — 3,4,5-F₃ CF₃ G²-7 — 3,5-Cl₂-4-F CF₃ G²-4 4-C(O)NHCH₂CF₃ 3,5-Cl₂-4-F CF₃ G²-6 — 3,5-Cl₂-4-F CF₃ G²-7 — 3,5-Cl₂-4-F CF₃ G²-9 — 3,5-Cl₂-4-F CF₃ G²-10 — 3,5-Cl₂-4-F CF₃ G²-10 CH₃ 3,5-Cl₂-4-F CF₂Cl G²-7 — 3,4,5-Cl₃ CF₃ G²-4 4-C(O)NHCH₂CF₃ 3,4,5-Cl₃ CF₃ G²-6 — 3,4,5-Cl₃ CF₃ G²-7 — 3,4,5-Cl₃ CF₃ G²-9 — 3,4,5-Cl₃ CF₃ G²-10 — 3,4,5-Cl₃ CF₃ G²-10 CH₃ 3,4,5-Cl₃ CF₂Cl G²-7 — 3,5-Br₂-4-F CF₃ G²-4 4-C(O)NHCH₂CF₃ 3,5-Br₂-4-F CF₃ G²-6 — 3,5-Br₂-4-F CF₃ G²-7 — 3,5-Br₂-4-F CF₃ G²-9 — 3,5-Br₂-4-F CF₃ G²-10 — 3,5-Br₂-4-F CF₃ G²-10 CH₃ 3,5-Br₂-4-F CF₂Cl G²-7 — 3,4,5-Br₃ CF₃ G²-7 — 3,4-F₂-5-CF₃ CF₃ G²-4 4-C(O)NHCH₂CF₃ 3,4-F₂-5-CF₃ CF₃ G²-6 — 3,4-F₂-5-CF₃ CF₃ G²-7 — 3,4-F₂-5-CF₃ CF₃ G²-9 — 3,4-F₂-5-CF₃ CF₃ G²-10 — 3,4-F₂-5-CF₃ CF₃ G²-10 CH₃ 3,4-F₂-5-CF₃ CF₂Cl G²-7 — 3-Cl-4-F-5-CF₃ CF₃ G²-4 4-C(O)NHCH₂CF₃ 3-Cl-4-F-5-CF₃ CF₃ G²-6 — 3-Cl-4-F-5-CF₃ CF₃ G²-7 — 3-Cl-4-F-5-CF₃ CF₃ G²-9 — 3-Cl-4-F-5-CF₃ CF₃ G²-10 — 3-Cl-4-F-5-CF₃ CF₃ G²-10 CH₃ 3-Cl-4-F-5-CF₃ CF₂Cl G²-7 — 3,4-Cl₂-5-CF₃ CF₃ G²-4 4-C(O)NHCH₂CF₃ 3,4-Cl₂-5-CF₃ CF₃ G²-6 — 3,4-Cl₂-5-CF₃ CF₃ G²-7 — 3,4-Cl₂-5-CF₃ CF₃ G²-9 — 3,4-Cl₂-5-CF₃ CF₃ G²-10 — 3,4-Cl₂-5-CF₃ CF₃ G²-10 CH₃ 3,4-Cl₂-5-CF₃ CF₂Cl G²-7 — 3,5-(CF₃)₂-4-Cl CF₃ G²-4 4-C(O)NHCH₂CF₃ 3,5-(CF₃)₂-4-Cl CF₃ G²-6 — 3,5-(CF₃)₂-4-Cl CF₃ G²-7 — 3,5-(CF₃)₂-4-Cl CF₃ G²-9 — 3,5-(CF₃)₂-4-Cl CF₃ G²-10 — 3,5-(CF₃)₂-4-Cl CF₃ G²-10 CH₃ 3,5-(CF₃)₂-4-Cl CF₂Cl G²-7 — 3,5-Cl₂-4-OCHF₂ CF₃ G²-7 — 3,5-Br₂-4-OCHF₂ CF₃ G²-7 —

Specific examples of the production intermediates or active compounds represented by Structure Formulae [3]-1 to [3]-90 and [4]-1 to [4]-18 included in the present invention include compounds shown in Table 6. However, the compounds in Table 6 are only for exemplification and the present invention is not limited to these compounds.

TABLE 6

[3]-1 

[3]-2 

[3]-3 

[3]-4 

[3]-5 

[3]-6 

[3]-7 

[3]-8 

[3]-9 

[3]-10

[3]-11

[3]-12

[3]-13

[3]-14

[3]-15

[3]-16

[3]-17

[3]-18

[3]-19

[3]-20

[3]-21

[3]-22

[3]-23

[3]-24

[3]-25

[3]-26

[3]-27

[3]-28

[3]-29

[3]-30

[3]-31

[3]-32

[3]-33

[3]-34

[3]-35

[3]-36

[3]-37

[3]-38

[3]-39

[3]-40

[3]-41

[3]-42

[3]-43

[3]-44

[3]-45

[3]-46

[3]-47

[3]-48

[3]-49

[3]-50

[3]-51

[3]-52

[3]-53

[3]-54

[3]-55

[3]-56

[3]-57

[3]-58

[3]-59

[3]-60

[3]-61

[3]-62

[3]-63

[3]-64

[3]-65

[3]-66

[3]-67

[3]-68

[3]-69

[3]-70

[3]-71

[3]-72

[3]-73

[3]-74

[3]-75

[3]-76

[3]-77

[3]-78

[3]-79

[3]-80

[3]-81

[3]-82

[3]-83

[3]-84

[3]-85

[3]-86

[3]-87

[3]-88

[3]-89

[3]-90

[4]-1 

[4]-2 

[4]-3 

[4]-4 

[4]-5 

[4]-6 

[4]-7 

[4]-8 

[4]-9 

[4]-10

[4]-11

[4]-12

[4]-13

[4]-14

[4]-15

[4]-16

[4]-17

[4]-18

In Table, the number representing the substitution site of the substituent X¹ and (X²)_(m1) corresponds to the site indicated by the number in each of Structure Formulae [1]-1 to [1]-110 and [2]-1 to [2]-75.

Furthermore, in Table, aromatic heterocyclic rings represented by D7-1a, D11-1a and D22-1a represent the following structures.

Moreover, in Table, the description of Et represents an ethyl group and t-Bu and Bu-t represent a tertiary butyl group.

X¹, (X²)_(ml) R³ Q X¹, (X²)_(ml) R³ Q 3-Br CF₃ CN 3,5-(CF₃)₂ CF₃ CH(CH₃)NH₂ 3-Br CF₃ C(O)OH 3,5-(CF₃)₂ CF₃ CH(CN)NH₂ 3-Br CF₃ C(O)OCH₃ 3,5-(CF₃)₂ CF₃ CHO 3-Br CF₃ C(O)Cl 3,5-(CF₃)₂ CF₃ C(O)CH₃ 3-Br CF₃ NO₂ 3,5-(CF₃)₂ CF₃ CN 3-I CF₃ CN 3,5-(CF₃)₂ CF₃ C(O)OH 3-I CF₃ C(O)OH 3,5-(CF₃)₂ CF₃ C(O)OCH₃ 3-I CF₃ C(O)OCH₃ 3,5-(CF₃)₂ CF₃ C(O)OEt 3-I CF₃ C(O)OEt 3,5-(CF₃)₂ CF₃ C(O)OBu-t 3-I CF₃ C(O)Cl 3,5-(CF₃)₂ CF₃ C(O)Cl 3-I CF₃ NO₂ 3,5-(CF₃)₂ CF₃ C(O)(D7-1a) 3-I CF₃ NH₂ 3,5-(CF₃)₂ CF₃ C(O)(D11-1a) 3-I CF₃ SCH₃ 3,5-(CF₃)₂ CF₃ C(O)(D22-1a) 3-I CF₃ S(O)CH₃ 3,5-(CF₃)₂ CF₃ NO₂ 3-I CF₃ SO₂CH₃ 3,5-(CF₃)₂ CF₃ NH₂ 3-CF₃ CF₃ CN 3,5-(CF₃)₂ CF₃ OH 3-CF₃ CF₃ C(O)OH 3,5-(CF₃)₂ CF₃ OCH₃ 3-CF₃ CF₃ C(O)OCH₃ 3,5-(CF₃)₂ CF₃ OCF₃ 3-CF₃ CF₃ C(O)OEt 3,5-(CF₃)₂ CF₃ OSO₂CH₃ 3-CF₃ CF₃ C(O)Cl 3,5-(CF₃)₂ CF₃ OSO₂CF₃ 3-CF₃ CF₃ NO₂ 3,5-(CF₃)₂ CF₃ SCH₃ 3-CF₃ CF₃ NH₂ 3,5-(CF₃)₂ CF₃ S(O)CH₃ 3-CF₃ CF₃ SCH₃ 3,5-(CF₃)₂ CF₃ SO₂CH₃ 3-CF₃ CF₃ S(O)CH₃ 3,5-(CF₃)₂ CF₂Cl CN 3-CF₃ CF₃ SO₂CH₃ 3,5-(CF₃)₂ CF₂Cl C(O)OH 3-CF₂CF₃ CF₃ CN 3,5-(CF₃)₂ CF₂Cl C(O)OCH₃ 3-CF₂CF₃ CF₃ C(O)OH 3,5-(CF₃)₂ CF₂Cl C(O)OEt 3-CF₂CF₃ CF₃ C(O)OCH₃ 3,5-(CF₃)₂ CF₂Cl C(O)Cl 3-CF₂CF₃ CF₃ C(O)Cl 3,5-(CF₃)₂ CF₂Cl NO₂ 3-CF₂CF₃ CF₃ NO₂ 3,5-(CF₃)₂ CF₂Cl NH₂ 3-OCF₃ CF₃ CN 3,5-(CF₃)₂ CF₂Cl SCH₃ 3-OCF₃ CF₃ C(O)OH 3,5-(CF₃)₂ CF₂Cl S(O)CH₃ 3-OCF₃ CF₃ C(O)OCH₃ 3,5-(CF₃)₂ CF₂Cl SO₂CH₃ 3-OCF₃ CF₃ C(O)Cl 3-Cl-5-OCHF₂ CF₃ CN 3-OCF₃ CF₃ NO₂ 3-Cl-5-OCHF₂ CF₃ C(O)OH 3-SCF₃ CF₃ CN 3-Cl-5-OCHF₂ CF₃ C(O)OCH₃ 3-SCF₃ CF₃ C(O)OH 3-Cl-5-OCHF₂ CF₃ C(O)OEt 3-SCF₃ CF₃ C(O)OCH₃ 3-Cl-5-OCHF₂ CF₃ C(O)Cl 3-SCF₃ CF₃ C(O)Cl 3-Cl-5-OCHF₂ CF₃ NO₂ 3-SCF₃ CF₃ NO₂ 3-Cl-5-OCHF₂ CF₃ NH₂ 3-SF₅ CF₃ CN 3-Cl-5-OCHF₂ CF₃ SCH₃ 3-SF₅ CF₃ C(O)OH 3-Cl-5-OCHF₂ CF₃ S(O)CH₃ 3-SF₅ CF₃ C(O)OCH₃ 3-Cl-5-OCHF₂ CF₃ SO₂CH₃ 3-SF₅ CF₃ C(O)Cl 3-Br-5-OCHF₂ CF₃ CN 3-SF₅ CF₃ NO₂ 3-Br-5-OCHF₂ CF₃ C(O)OH 3-Cl-4-F CF₃ CN 3-Br-5-OCHF₂ CF₃ C(O)OCH₃ 3-Cl-4-F CF₃ C(O)OH 3-Br-5-OCHF₂ CF₃ C(O)Cl 3-Cl-4-F CF₃ C(O)OCH₃ 3-Br-5-OCHF₂ CF₃ NO₂ 3-Cl-4-F CF₃ C(O)OEt 3-CF₃-5-OCHF₂ CF₃ CN 3-Cl-4-F CF₃ C(O)Cl 3-CF₃-5-OCHF₂ CF₃ C(O)OH 3-Cl-4-F CF₃ NO₂ 3-CF₃-5-OCHF₂ CF₃ C(O)OCH₃ 3-Cl-4-F CF₃ NH₂ 3-CF₃-5-OCHF₂ CF₃ C(O)Cl 3-Cl-4-F CF₃ SCH₃ 3-CF₃-5-OCHF₂ CF₃ NO₂ 3-Cl-4-F CF₃ S(O)CH₃ 3-Cl-5-OCF₃ CF₃ CN 3-Cl-4-F CF₃ SO₂CH₃ 3-Cl-5-OCF₃ CF₃ C(O)OH 3-F-5-Cl CF₃ CN 3-Cl-5-OCF₃ CF₃ C(O)OCH₃ 3-F-5-Cl CF₃ C(O)OH 3-Cl-5-OCF₃ CF₃ C(O)OEt 3-F-5-Cl CF₃ C(O)OCH₃ 3-Cl-5-OCF₃ CF₃ C(O)Cl 3-F-5-Cl CF₃ C(O)OEt 3-Cl-5-OCF₃ CF₃ NO₂ 3-F-5-Cl CF₃ C(O)Cl 3-Cl-5-OCF₃ CF₃ NH₂ 3-F-5-Cl CF₃ NO₂ 3-Cl-5-OCF₃ CF₃ SCH₃ 3-F-5-Cl CF₃ NH₂ 3-Cl-5-OCF₃ CF₃ S(O)CH₃ 3-F-5-Cl CF₃ SCH₃ 3-Cl-5-OCF₃ CF₃ SO₂CH₃ 3-F-5-Cl CF₃ S(O)CH₃ 3-Br-5-OCF₃ CF₃ CN 3-F-5-Cl CF₃ SO₂CH₃ 3-Br-5-OCF₃ CF₃ C(O)OH 3,4-Cl₂ CF₃ CN 3-Br-5-OCF₃ CF₃ C(O)OCH₃ 3,4-Cl₂ CF₃ C(O)OH 3-Br-5-OCF₃ CF₃ C(O)Cl 3,4-Cl₂ CF₃ C(O)OCH₃ 3-Br-5-OCF₃ CF₃ NO₂ 3,4-Cl₂ CF₃ C(O)OEt 3-CF₃-5-OCF₃ CF₃ CN 3,4-Cl₂ CF₃ C(O)Cl 3-CF₃-5-OCF₃ CF₃ C(O)OH 3,4-Cl₂ CF₃ NO₂ 3-CF₃-5-OCF₃ CF₃ C(O)OCH₃ 3,4-Cl₂ CF₃ NH₂ 3-CF₃-5-OCF₃ CF₃ C(O)Cl 3,4-Cl₂ CF₃ SCH₃ 3-CF₃-5-OCF₃ CF₃ NO₂ 3,4-Cl₂ CF₃ S(O)CH₃ 3-Cl-5-SCF₃ CF₃ CN 3,4-Cl₂ CF₃ SO₂CH₃ 3-Cl-5-SCF₃ CF₃ C(O)OH 3,5-Cl₂ CF₃ F 3-Cl-5-SCF₃ CF₃ C(O)OCH₃ 3,5-Cl₂ CF₃ Cl 3-Cl-5-SCF₃ CF₃ C(O)OEt 3,5-Cl₂ CF₃ Br 3-Cl-5-SCF₃ CF₃ C(O)Cl 3,5-Cl₂ CF₃ I 3-Cl-5-SCF₃ CF₃ NO₂ 3,5-Cl₂ CF₃ CH₃ 3-Cl-5-SCF₃ CF₃ NH₂ 3,5-Cl₂ CF₃ CF₃ 3-Cl-5-SCF₃ CF₃ SCH₃ 3,5-Cl₂ CF₃ CH₂OH 3-Cl-5-SCF₃ CF₃ S(O)CH₃ 3,5-Cl₂ CF₃ CH₂OC(O)CH₃ 3-Cl-5-SCF₃ CF₃ SO₂CH₃ 3,5-Cl₂ CF₃ CH₂NH₂ 3-Br-5-SCF₃ CF₃ CN 3,5-Cl₂ CF₃ CH(CH₃)NH₂ 3-Br-5-SCF₃ CF₃ C(O)OH 3,5-Cl₂ CF₃ CH(CN)NH₂ 3-Br-5-SCF₃ CF₃ C(O)OCH₃ 3,5-Cl₂ CF₃ CHO 3-Br-5-SCF₃ CF₃ C(O)Cl 3,5-Cl₂ CF₃ CN 3-Br-5-SCF₃ CF₃ NO₂ 3,5-Cl₂ CF₃ C(O)OH 3-CF₃-5-CN CF₃ CN 3,5-Cl₂ CF₃ C(O)OCH₃ 3-CF₃-5-CN CF₃ C(O)OH 3,5-Cl₂ CF₃ C(O)OEt 3-CF₃-5-CN CF₃ C(O)OCH₃ 3,5-Cl₂ CF₃ C(O)Cl 3-CF₃-5-CN CF₃ C(O)Cl 3,5-Cl₂ CF₃ C(O)(D7-1a) 3-CF₃-5-CN CF₃ NO₂ 3,5-Cl₂ CF₃ C(O)(D11-1a) 3,4,5-F₃ CF₃ CN 3,5-Cl₂ CF₃ C(O)(D22-1a) 3,4,5-F₃ CF₃ C(O)OH 3,5-Cl₂ CF₃ NO₂ 3,4,5-F₃ CF₃ C(O)OCH₃ 3,5-Cl₂ CF₃ NH₂ 3,4,5-F₃ CF₃ C(O)Cl 3,5-Cl₂ CF₃ OCF₃ 3,4,5-F₃ CF₃ NO₂ 3,5-Cl₂ CF₃ OSO₂CF₃ 3,5-Cl₂-4-F CF₃ F 3,5-Cl₂ CF₃ SCH₃ 3,5-Cl₂-4-F CF₃ Cl 3,5-Cl₂ CF₃ S(O)CH₃ 3,5-Cl₂-4-F CF₃ Br 3,5-Cl₂ CF₃ SO₂CH₃ 3,5-Cl₂-4-F CF₃ I 3,5-Cl₂ CF₂Cl CN 3,5-Cl₂-4-F CF₃ CH₃ 3,5-Cl₂ CF₂Cl C(O)OH 3,5-Cl₂-4-F CF₃ CF₃ 3,5-Cl₂ CF₂Cl C(O)OCH₃ 3,5-Cl₂-4-F CF₃ CH₂OH 3,5-Cl₂ CF₂Cl C(O)Cl 3,5-Cl₂-4-F CF₃ CH₂OC(O)CH₃ 3,5-Cl₂ CF₂Cl NO₂ 3,5-Cl₂-4-F CF₃ CH₂NH₂ 3-Br-4-F CF₃ CN 3,5-Cl₂-4-F CF₃ CH(CH₃)NH₂ 3-Br-4-F CF₃ C(O)OH 3,5-Cl₂-4-F CF₃ CH(CN)NH₂ 3-Br-4-F CF₃ C(O)OCH₃ 3,5-Cl₂-4-F CF₃ CHO 3-Br-4-F CF₃ C(O)OEt 3,5-Cl₂-4-F CF₃ CN 3-Br-4-F CF₃ C(O)Cl 3,5-Cl₂-4-F CF₃ C(O)OH 3-Br-4-F CF₃ NO₂ 3,5-Cl₂-4-F CF₃ C(O)OCH₃ 3-Br-4-F CF₃ NH₂ 3,5-Cl₂-4-F CF₃ C(O)OEt 3-Br-4-F CF₃ SCH₃ 3,5-Cl₂-4-F CF₃ C(O)Cl 3-Br-4-F CF₃ S(O)CH₃ 3,5-Cl₂-4-F CF₃ C(O)(D7-1a) 3-Br-4-F CF₃ SO₂CH₃ 3,5-Cl₂-4-F CF₃ C(O)(D11-1a) 3-F-5-Br CF₃ CN 3,5-Cl₂-4-F CF₃ C(O)(D22-1a) 3-F-5-Br CF₃ C(O)OH 3,5-Cl₂-4-F CF₃ NO₂ 3-F-5-Br CF₃ C(O)OCH₃ 3,5-Cl₂-4-F CF₃ NH₂ 3-F-5-Br CF₃ C(O)OEt 3,5-Cl₂-4-F CF₃ OCF₃ 3-F-5-Br CF₃ C(O)Cl 3,5-Cl₂-4-F CF₃ OSO₂CF₃ 3-F-5-Br CF₃ NO₂ 3,5-Cl₂-4-F CF₃ SCH₃ 3-F-5-Br CF₃ NH₂ 3,5-Cl₂-4-F CF₃ S(O)CH₃ 3-F-5-Br CF₃ SCH₃ 3,5-Cl₂-4-F CF₃ SO₂CH₃ 3-F-5-Br CF₃ S(O)CH₃ 3,5-Cl₂-4-F CF₂Cl CN 3-F-5-Br CF₃ SO₂CH₃ 3,5-Cl₂-4-F CF₂Cl C(O)OH 3-Br-4-Cl CF₃ CN 3,5-Cl₂-4-F CF₂Cl C(O)OCH₃ 3-Br-4-Cl CF₃ C(O)OH 3,5-Cl₂-4-F CF₂Cl C(O)Cl 3-Br-4-Cl CF₃ C(O)OCH₃ 3,5-Cl₂-4-F CF₂Cl NO₂ 3-Br-4-Cl CF₃ C(O)Cl 3,4,5-Cl₃ CF₃ F 3-Br-4-Cl CF₃ NO₂ 3,4,5-Cl₃ CF₃ Cl 3-Cl-4-Br CF₃ CN 3,4,5-Cl₃ CF₃ Br 3-Cl-4-Br CF₃ C(O)OH 3,4,5-Cl₃ CF₃ I 3-Cl-4-Br CF₃ C(O)OCH₃ 3,4,5-Cl₃ CF₃ CH₃ 3-Cl-4-Br CF₃ C(O)Cl 3,4,5-Cl₃ CF₃ CF₃ 3-Cl-4-Br CF₃ NO₂ 3,4,5-Cl₃ CF₃ CH₂OH 3-Cl-5-Br CF₃ F 3,4,5-Cl₃ CF₃ CH₂OC(O)CH₃ 3-Cl-5-Br CF₃ Cl 3,4,5-Cl₃ CF₃ CH₂NH₂ 3-Cl-5-Br CF₃ Br 3,4,5-Cl₃ CF₃ CH(CH₃)NH₂ 3-Cl-5-Br CF₃ I 3,4,5-Cl₃ CF₃ CH(CN)NH₂ 3-Cl-5-Br CF₃ CH₃ 3,4,5-Cl₃ CF₃ CHO 3-Cl-5-Br CF₃ CF₃ 3,4,5-Cl₃ CF₃ CN 3-Cl-5-Br CF₃ CH₂OH 3,4,5-Cl₃ CF₃ C(O)OH 3-Cl-5-Br CF₃ CH₂OC(O)CH₃ 3,4,5-Cl₃ CF₃ C(O)OCH₃ 3-Cl-5-Br CF₃ CH₂NH₂ 3,4,5-Cl₃ CF₃ C(O)OEt 3-Cl-5-Br CF₃ CH(CH₃)NH₂ 3,4,5-Cl₃ CF₃ C(O)Cl 3-Cl-5-Br CF₃ CH(CN)NH₂ 3,4,5-Cl₃ CF₃ C(O)(D7-1a) 3-Cl-5-Br CF₃ CHO 3,4,5-Cl₃ CF₃ C(O)(D11-1a) 3-Cl-5-Br CF₃ CN 3,4,5-Cl₃ CF₃ C(O)(D22-1a) 3-Cl-5-Br CF₃ C(O)OH 3,4,5-Cl₃ CF₃ NO₂ 3-Cl-5-Br CF₃ C(O)OCH₃ 3,4,5-Cl₃ CF₃ NH₂ 3-Cl-5-Br CF₃ C(O)OEt 3,4,5-Cl₃ CF₃ OCF₃ 3-Cl-5-Br CF₃ C(O)Cl 3,4,5-Cl₃ CF₃ OSO₂CF₃ 3-Cl-5-Br CF₃ C(O)(D7-1a) 3,4,5-Cl₃ CF₃ SCH₃ 3-Cl-5-Br CF₃ C(O)(D11-1a) 3,4,5-Cl₃ CF₃ S(O)CH₃ 3-Cl-5-Br CF₃ C(O)(D22-1a) 3,4,5-Cl₃ CF₃ SO₂CH₃ 3-Cl-5-Br CF₃ NO₂ 3,4,5-Cl₃ CF₂Cl CN 3-Cl-5-Br CF₃ NH₂ 3,4,5-Cl₃ CF₂Cl C(O)OH 3-Cl-5-Br CF₃ OCF₃ 3,4,5-Cl₃ CF₂Cl C(O)OCH₃ 3-Cl-5-Br CF₃ OSO₂CF₃ 3,4,5-Cl₃ CF₂Cl C(O)Cl 3-Cl-5-Br CF₃ SCH₃ 3,4,5-Cl₃ CF₂Cl NO₂ 3-Cl-5-Br CF₃ S(O)CH₃ 3,5-Br₂-4-F CF₃ F 3-Cl-5-Br CF₃ SO₂CH₃ 3,5-Br₂-4-F CF₃ Cl 3-Cl-5-Br CF₂Cl CN 3,5-Br₂-4-F CF₃ Br 3-Cl-5-Br CF₂Cl C(O)OH 3,5-Br₂-4-F CF₃ I 3-Cl-5-Br CF₂Cl C(O)OCH₃ 3,5-Br₂-4-F CF₃ CH₃ 3-Cl-5-Br CF₂Cl C(O)Cl 3,5-Br₂-4-F CF₃ CF₃ 3-Cl-5-Br CF₂Cl NO₂ 3,5-Br₂-4-F CF₃ CH₂OH 3,4-Br₂ CF₃ CN 3,5-Br₂-4-F CF₃ CH₂OC(O)CH₃ 3,4-Br₂ CF₃ C(O)OH 3,5-Br₂-4-F CF₃ CH₂NH₂ 3,4-Br₂ CF₃ C(O)OCH₃ 3,5-Br₂-4-F CF₃ CH(CH₃)NH₂ 3,4-Br₂ CF₃ C(O)Cl 3,5-Br₂-4-F CF₃ CH(CN)NH₂ 3,4-Br₂ CF₃ NO₂ 3,5-Br₂-4-F CF₃ CHO 3,5-Br₂ CF₃ F 3,5-Br₂-4-F CF₃ CN 3,5-Br₂ CF₃ Cl 3,5-Br₂-4-F CF₃ C(O)OH 3,5-Br₂ CF₃ Br 3,5-Br₂-4-F CF₃ C(O)OCH₃ 3,5-Br₂ CF₃ I 3,5-Br₂-4-F CF₃ C(O)OEt 3,5-Br₂ CF₃ CH₃ 3,5-Br₂-4-F CF₃ C(O)Cl 3,5-Br₂ CF₃ CF₃ 3,5-Br₂-4-F CF₃ C(O)(D7-1a) 3,5-Br₂ CF₃ CH₂OH 3,5-Br₂-4-F CF₃ C(O)(D11-1a) 3,5-Br₂ CF₃ CH₂OC(O)CH₃ 3,5-Br₂-4-F CF₃ C(O)(D22-1a) 3,5-Br₂ CF₃ CH₂NH₂ 3,5-Br₂-4-F CF₃ NO₂ 3,5-Br₂ CF₃ CH(CH₃)NH₂ 3,5-Br₂-4-F CF₃ NH₂ 3,5-Br₂ CF₃ CH(CN)NH₂ 3,5-Br₂-4-F CF₃ OCF₃ 3,5-Br₂ CF₃ CHO 3,5-Br₂-4-F CF₃ OSO₂CF₃ 3,5-Br₂ CF₃ CN 3,5-Br₂-4-F CF₃ SCH₃ 3,5-Br₂ CF₃ C(O)OH 3,5-Br₂-4-F CF₃ S(O)CH₃ 3,5-Br₂ CF₃ C(O)OCH₃ 3,5-Br₂-4-F CF₃ SO₂CH₃ 3,5-Br₂ CF₃ C(O)OEt 3,5-Br₂-4-F CF₂Cl CN 3,5-Br₂ CF₃ C(O)Cl 3,5-Br₂-4-F CF₂Cl C(O)OH 3,5-Br₂ CF₃ C(O)(D7-1a) 3,5-Br₂-4-F CF₂Cl C(O)OCH₃ 3,5-Br₂ CF₃ C(O)(D11-1a) 3,5-Br₂-4-F CF₂Cl C(O)Cl 3,5-Br₂ CF₃ C(O)(D22-1a) 3,5-Br₂-4-F CF₂Cl NO₂ 3,5-Br₂ CF₃ NO₂ 3,4,5-Br₃ CF₃ CN 3,5-Br₂ CF₃ NH₂ 3,4,5-Br₃ CF₃ C(O)OH 3,5-Br₂ CF₃ OCF₃ 3,4,5-Br₃ CF₃ C(O)OCH₃ 3,5-Br₂ CF₃ OSO₂CF₃ 3,4,5-Br₃ CF₃ C(O)Cl 3,5-Br₂ CF₃ SCH₃ 3,4,5-Br₃ CF₃ NO₂ 3,5-Br₂ CF₃ S(O)CH₃ 3,4-F₂-5-CF₃ CF₃ F 3,5-Br₂ CF₃ SO₂CH₃ 3,4-F₂-5-CF₃ CF₃ Cl 3,5-Br₂ CF₂Cl CN 3,4-F₂-5-CF₃ CF₃ Br 3,5-Br₂ CF₂Cl C(O)OH 3,4-F₂-5-CF₃ CF₃ I 3,5-Br₂ CF₂Cl C(O)OCH₃ 3,4-F₂-5-CF₃ CF₃ CH₃ 3,5-Br₂ CF₂Cl C(O)Cl 3,4-F₂-5-CF₃ CF₃ CF₃ 3,5-Br₂ CF₂Cl NO₂ 3,4-F₂-5-CF₃ CF₃ CH₂OH 3-I-4-F CF₃ CN 3,4-F₂-5-CF₃ CF₃ CH₂OC(O)CH₃ 3-I-4-F CF₃ C(O)OH 3,4-F₂-5-CF₃ CF₃ CH₂NH₂ 3-I-4-F CF₃ C(O)OCH₃ 3,4-F₂-5-CF₃ CF₃ CH(CH₃)NH₂ 3-I-4-F CF₃ C(O)Cl 3,4-F₂-5-CF₃ CF₃ CH(CN)NH₂ 3-I-4-F CF₃ NO₂ 3,4-F₂-5-CF₃ CF₃ CHO 3-F-5-I CF₃ CN 3,4-F₂-5-CF₃ CF₃ CN 3-F-5-I CF₃ C(O)OH 3,4-F₂-5-CF₃ CF₃ C(O)OH 3-F-5-I CF₃ C(O)OCH₃ 3,4-F₂-5-CF₃ CF₃ C(O)OCH₃ 3-F-5-I CF₃ C(O)Cl 3,4-F₂-5-CF₃ CF₃ C(O)OEt 3-F-5-I CF₃ NO₂ 3,4-F₂-5-CF₃ CF₃ C(O)Cl 3-Cl-5-I CF₃ CN 3,4-F₂-5-CF₃ CF₃ C(O)(D7-1a) 3-Cl-5-I CF₃ C(O)OH 3,4-F₂-5-CF₃ CF₃ C(O)(D11-1a) 3-Cl-5-I CF₃ C(O)OCH₃ 3,4-F₂-5-CF₃ CF₃ C(O)(D22-1a) 3-Cl-5-I CF₃ C(O)OEt 3,4-F₂-5-CF₃ CF₃ NO₂ 3-Cl-5-I CF₃ C(O)Cl 3,4-F₂-5-CF₃ CF₃ NH₂ 3-Cl-5-I CF₃ NO₂ 3,4-F₂-5-CF₃ CF₃ OCF₃ 3-Cl-5-I CF₃ NH₂ 3,4-F₂-5-CF₃ CF₃ OSO₂CF₃ 3-Cl-5-I CF₃ SCH₃ 3,4-F₂-5-CF₃ CF₃ SCH₃ 3-Cl-5-I CF₃ S(O)CH₃ 3,4-F₂-5-CF₃ CF₃ S(O)CH₃ 3-Cl-5-I CF₃ SO₂CH₃ 3,4-F₂-5-CF₃ CF₃ SO₂CH₃ 3-CF₃-4-F CF₃ CN 3,4-F₂-5-CF₃ CF₂Cl CN 3-CF₃-4-F CF₃ C(O)OH 3,4-F₂-5-CF₃ CF₂Cl C(O)OH 3-CF₃-4-F CF₃ C(O)OCH₃ 3,4-F₂-5-CF₃ CF₂Cl C(O)OCH₃ 3-CF₃-4-F CF₃ C(O)OEt 3,4-F₂-5-CF₃ CF₂Cl C(O)Cl 3-CF₃-4-F CF₃ C(O)Cl 3,4-F₂-5-CF₃ CF₂Cl NO₂ 3-CF₃-4-F CF₃ NO₂ 3-Cl-4-F-5-CF₃ CF₃ F 3-CF₃-4-F CF₃ NH₂ 3-Cl-4-F-5-CF₃ CF₃ Cl 3-CF₃-4-F CF₃ SCH₃ 3-Cl-4-F-5-CF₃ CF₃ Br 3-CF₃-4-F CF₃ S(O)CH₃ 3-Cl-4-F-5-CF₃ CF₃ I 3-CF₃-4-F CF₃ SO₂CH₃ 3-Cl-4-F-5-CF₃ CF₃ CH₃ 3-F-5-CF₃ CF₃ CN 3-Cl-4-F-5-CF₃ CF₃ CF₃ 3-F-5-CF₃ CF₃ C(O)OH 3-Cl-4-F-5-CF₃ CF₃ CH₂OH 3-F-5-CF₃ CF₃ C(O)OCH₃ 3-Cl-4-F-5-CF₃ CF₃ CH₂OC(O)CH₃ 3-F-5-CF₃ CF₃ C(O)OEt 3-Cl-4-F-5-CF₃ CF₃ CH₂NH₂ 3-F-5-CF₃ CF₃ C(O)Cl 3-Cl-4-F-5-CF₃ CF₃ CH(CH₃)NH₂ 3-F-5-CF₃ CF₃ NO₂ 3-Cl-4-F-5-CF₃ CF₃ CH(C)NH₂ 3-F-5-CF₃ CF₃ NH₂ 3-Cl-4-F-5-CF₃ CF₃ CHO 3-F-5-CF₃ CF₃ SCH₃ 3-Cl-4-F-5-CF₃ CF₃ CN 3-F-5-CF₃ CF₃ S(O)CH₃ 3-Cl-4-F-5-CF₃ CF₃ C(O)OH 3-F-5-CF₃ CF₃ SO₂CH₃ 3-Cl-4-F-5-CF₃ CF₃ C(O)OCH₃ 3-CF₃-4-Cl CF₃ CN 3-Cl-4-F-5-CF₃ CF₃ C(O)OEt 3-CF₃-4-Cl CF₃ C(O)OH 3-Cl-4-F-5-CF₃ CF₃ C(O)Cl 3-CF₃-4-Cl CF₃ C(O)OCH₃ 3-Cl-4-F-5-CF₃ CF₃ C(O)(D7-1a) 3-CF₃-4-Cl CF₃ C(O)OEt 3-Cl-4-F-5-CF₃ CF₃ C(O)(D11-1a) 3-CF₃-4-Cl CF₃ C(O)Cl 3-Cl-4-F-5-CF₃ CF₃ C(O)(D22-1a) 3-CF₃-4-Cl CF₃ NO₂ 3-Cl-4-F-5-CF₃ CF₃ NO₂ 3-CF₃-4-Cl CF₃ NH₂ 3-Cl-4-F-5-CF₃ CF₃ NH₂ 3-CF₃-4-Cl CF₃ SCH₃ 3-Cl-4-F-5-CF₃ CF₃ OCF₃ 3-CF₃-4-Cl CF₃ S(O)CH₃ 3-Cl-4-F-5-CF₃ CF₃ OSO₂CF₃ 3-CF₃-4-Cl CF₃ SO₂CH₃ 3-Cl-4-F-5-CF₃ CF₃ SCH₃ 3-Cl-5-CF₃ CF₃ F 3-Cl-4-F-5-CF₃ CF₃ S(O)CH₃ 3-Cl-5-CF₃ CF₃ Cl 3-Cl-4-F-5-CF₃ CF₃ SO₂CH₃ 3-Cl-5-CF₃ CF₃ Br 3-Cl-4-F-5-CF₃ CF₂Cl CN 3-Cl-5-CF₃ CF₃ I 3-Cl-4-F-5-CF₃ CF₂Cl C(O)OH 3-Cl-5-CF₃ CF₃ CH₃ 3-Cl-4-F-5-CF₃ CF₂Cl C(O)OCH₃ 3-Cl-5-CF₃ CF₃ CF₃ 3-Cl-4-F-5-CF₃ CF₂Cl C(O)Cl 3-Cl-5-CF₃ CF₃ CH₂OH 3-Cl-4-F-5-CF₃ CF₂Cl NO₂ 3-Cl-5-CF₃ CF₃ CH₂OC(O)CH₃ 3,4-Cl₂-5-CF₃ CF₃ F 3-Cl-5-CF₃ CF₃ CH₂NH₂ 3,4-Cl₂-5-CF₃ CF₃ Cl 3-Cl-5-CF₃ CF₃ CH(CH₃)NH₂ 3,4-Cl₂-5-CF₃ CF₃ Br 3-Cl-5-CF₃ CF₃ CH(CN)NH₂ 3,4-Cl₂-5-CF₃ CF₃ I 3-Cl-5-CF₃ CF₃ CHO 3,4-Cl₂-5-CF₃ CF₃ CH₃ 3-Cl-5-CF₃ CF₃ CN 3,4-Cl₂-5-CF₃ CF₃ CF₃ 3-Cl-5-CF₃ CF₃ C(O)OH 3,4-Cl₂-5-CF₃ CF₃ CH₂OH 3-Cl-5-CF₃ CF₃ C(O)OCH₃ 3,4-Cl₂-5-CF₃ CF₃ CH₂OC(O)CH₃ 3-Cl-5-CF₃ CF₃ C(O)OEt 3,4-Cl₂-5-CF₃ CF₃ CH₂NH₂ 3-Cl-5-CF₃ CF₃ C(O)Cl 3,4-Cl₂-5-CF₃ CF₃ CH(CH₃)NH₂ 3-Cl-5-CF₃ CF₃ C(O)(D7-1a) 3,4-Cl₂-5-CF₃ CF₃ CH(CN)NH₂ 3-Cl-5-CF₃ CF₃ C(O)(D11-1a) 3,4-Cl₂-5-CF₃ CF₃ CHO 3-Cl-5-CF₃ CF₃ C(O)(D22-1a) 3,4-Cl₂-5-CF₃ CF₃ CN 3-Cl-5-CF₃ CF₃ NO₂ 3,4-Cl₂-5-CF₃ CF₃ C(O)OH 3-Cl-5-CF₃ CF₃ NH₂ 3,4-Cl₂-5-CF₃ CF₃ C(O)OCH₃ 3-Cl-5-CF₃ CF₃ OCF₃ 3,4-Cl₂-5-CF₃ CF₃ C(O)OEt 3-Cl-5-CF₃ CF₃ OSO₂CF₃ 3,4-Cl₂-5-CF₃ CF₃ C(O)Cl 3-Cl-5-CF₃ CF₃ SCH₃ 3,4-Cl₂-5-CF₃ CF₃ C(O)(D7-1a) 3-Cl-5-CF₃ CF₃ S(O)CH₃ 3,4-Cl₂-5-CF₃ CF₃ C(O)(D11-a) 3-Cl-5-CF₃ CF₃ SO₂CH₃ 3,4-Cl₂-5-CF₃ CF₃ C(O)(D22-1a) 3-Cl-5-CF₃ CF₂Cl CN 3,4-Cl₂-5-CF₃ CF₃ NO₂ 3-Cl-5-CF₃ CF₂Cl C(O)OH 3,4-Cl₂-5-CF₃ CF₃ NH₂ 3-Cl-5-CF₃ CF₂Cl C(O)OCH₃ 3,4-Cl₂-5-CF₃ CF₃ OCF₃ 3-Cl-5-CF₃ CF₂Cl C(O)Cl 3,4-Cl₂-5-CF₃ CF₃ OSO₂CF₃ 3-Cl-5-CF₃ CF₂Cl NO₂ 3,4-Cl₂-5-CF₃ CF₃ SCH₃ 3-Br-5-CF₃ CF₃ F 3,4-Cl₂-5-CF₃ CF₃ S(O)CH₃ 3-Br-5-CF₃ CF₃ Cl 3,4-Cl₂-5-CF₃ CF₃ SO₂CH₃ 3-Br-5-CF₃ CF₃ Br 3,4-Cl₂-5-CF₃ CF₂Cl CN 3-Br-5-CF₃ CF₃ I 3,4-Cl₂-5-CF₃ CF₂Cl C(O)OH 3-Br-5-CF₃ CF₃ CH₃ 3,4-Cl₂-5-CF₃ CF₂Cl C(O)OCH₃ 3-Br-5-CF₃ CF₃ CF₃ 3,4-Cl₂-5-CF₃ CF₂Cl C(O)Cl 3-Br-5-CF₃ CF₃ CH₂OH 3,4-Cl₂-5-CF₃ CF₂Cl NO₂ 3-Br-5-CF₃ CF₃ CH₂OC(O)CH₃ 3,5-(CF₃)₂-4-Cl CF₃ F 3-Br-5-CF₃ CF₃ CH₂NH₂ 3,5-(CF₃)₂-4-Cl CF₃ Cl 3-Br-5-CF₃ CF₃ CH(CH₃)NH₂ 3,5-(CF₃)₂-4-Cl CF₃ Br 3-Br-5-CF₃ CF₃ CH(CN)NH₂ 3,5-(CF₃)₂-4-Cl CF₃ I 3-Br-5-CF₃ CF₃ CHO 3,5-(CF₃)₂-4-Cl CF₃ CH₃ 3-Br-5-CF₃ CF₃ CN 3,5-(CF₃)₂-4-Cl CF₃ CF₃ 3-Br-5-CF₃ CF₃ C(O)OH 3,5-(CF₃)₂-4-Cl CF₃ CH₂OH 3-Br-5-CF₃ CF₃ C(O)OCH₃ 3,5-(CF₃)₂-4-Cl CF₃ CH₂OC(O)CH₃ 3-Br-5-CF₃ CF₃ C(O)OEt 3,5-(CF₃)₂-4-Cl CF₃ CH₂NH₂ 3-Br-5-CF₃ CF₃ C(O)Cl 3,5-(CF₃)₂-4-Cl CF₃ CH(CH₃)NH₂ 3-Br-5-CF₃ CF₃ C(O)(D7-1a) 3,5-(CF₃)₂-4-Cl CF₃ CH(CN)NH₂ 3-Br-5-CF₃ CF₃ C(O)(D11-1a) 3,5-(CF₃)₂-4-Cl CF₃ CHO 3-Br-5-CF₃ CF₃ C(O)(D22-1a) 3,5-(CF₃)₂-4-Cl CF₃ CN 3-Br-5-CF₃ CF₃ NO₂ 3,5-(CF₃)₂-4-Cl CF₃ C(O)OH 3-Br-5-CF₃ CF₃ NH₂ 3,5-(CF₃)₂-4-Cl CF₃ C(O)OCH₃ 3-Br-5-CF₃ CF₃ OCF₃ 3,5-(CF₃)₂-4-Cl CF₃ C(O)OEt 3-Br-5-CF₃ CF₃ OSO₂CF₃ 3,5-(CF₃)₂-4-Cl CF₃ C(O)Cl 3-Br-5-CF₃ CF₃ SCH₃ 3,5-(CF₃)₂-4-Cl CF₃ C(O)(D7-1a) 3-Br-5-CF₃ CF₃ S(O)CH₃ 3,5-(CF₃)₂-4-Cl CF₃ C(O)(D11-1a) 3-Br-5-CF₃ CF₃ SO₂CH₃ 3,5-(CF₃)₂-4-Cl CF₃ C(O)(D22-1a) 3-Br-5-CF₃ CF₂Cl CN 3,5-(CF₃)₂-4-Cl CF₃ NO₂ 3-Br-5-CF₃ CF₂Cl C(O)OH 3,5-(CF₃)₂-4-Cl CF₃ NH₂ 3-Br-5-CF₃ CF₂Cl C(O)OCH₃ 3,5-(CF₃)₂-4-Cl CF₃ OCF₃ 3-Br-5-CF₃ CF₂Cl C(O)Cl 3,5-(CF₃)₂-4-Cl CF₃ OSO₂CF₃ 3-Br-5-CF₃ CF₂Cl NO₂ 3,5-(CF₃)₂-4-Cl CF₃ SCH₃ 3,5-(CF₃)₂ CF₃ F 3,5-(CF₃)₂-4-Cl CF₃ S(O)CH₃ 3,5-(CF₃)₂ CF₃ Cl 3,5-(CF₃)₂-4-Cl CF₃ SO₂CH₃ 3,5-(CF₃)₂ CF₃ Br 3,5-(CF₃)₂-4-Cl CF₂Cl CN 3,5-(CF₃)₂ CF₃ I 3,5-(CF₃)₂-4-Cl CF₂Cl C(O)OH 3,5-(CF₃)₂ CF₃ CH₃ 3,5-(CF₃)₂-4-Cl CF₂Cl C(O)OCH₃ 3,5-(CF₃)₂ CF₃ Et 3,5-(CF₃)₂-4-Cl CF₂Cl C(O)Cl 3,5-(CF₃)₂ CF₃ CH₂Cl 3,5-(CF₃)₂-4-Cl CF₂Cl NO₂ 3,5-(CF₃)₂ CF₃ CH₂Br 3,5-Cl₂-4-OCHF₂ CF₃ CN 3,5-(CF₃)₂ CF₃ CF₃ 3,5-Cl₂-4-OCHF₂ CF₃ C(O)OH 3,5-(CF₃)₂ CF₃ CH(CH₃)Cl 3,5-Cl₂-4-OCHF₂ CF₃ C(O)OCH₃ 3,5-(CF₃)₂ CF₃ CH(CH₃)Br 3,5-Cl₂-4-OCHF₂ CF₃ C(O)Cl 3,5-(CF₃)₂ CF₃ CH₂OH 3,5-Cl₂-4-OCHF₂ CF₃ NO₂ 3,5-(CF₃)₂ CF₃ CH₂OC(O)CH₃ 3,5-Br₂-4-OCHF₂ CF₃ CN 3,5-(CF₃)₂ CF₃ CH₂OSO₂CH₃ 3,5-Br₂-4-OCHF₂ CF₃ C(O)OH 3,5-(CF₃)₂ CF₃ CH₂OSO₂CF₃ 3,5-Br₂-4-OCHF₂ CF₃ C(O)OCH₃ 3,5-(CF₃)₂ CF₃ CH(CH₃)OH 3,5-Br₂-4-OCHF₂ CF₃ C(O)Cl 3,5-(CF₃)₂ CF₃ CH₂NH₂ 3,5-Br₂-4-OCHF₂ CF₃ NO₂

The compound of the present invention can effectively control with a low concentration thereof, any pests such as insects including so-called agricultural insect pests damaging agricultural or horticultural crops and trees, so-called domestic animal insect pests being parasitic in domestic animals/fowls, so-called sanitary insects adversely affecting in various manners, the living environment of the human such as the house and so-called stored grain insect pests damaging grains and the like stored in a warehouse; and mites, Crustacea, Mollusc and Nematoda which are generated and suffer damages in a situation similar to that in the case of the insects.

Specific examples of the insects, the mites, the Crustacea, the Mollusc and the Nematoda capable of being controlled using the compound of the present invention include:

Lepidopteran insects such as Adoxophyes honmai, Adoxophyes orana faciata, Archips breviplicanus, Archips fuscocupreanus, Grapholita molesta, Homona magnanima, Leguminivora glycinivorella, Matsumuraeses phaseoli, Pandemis heparana, Bucculatrix pyrivorella, Lyonetia clerkella, Lyonetia prunifoliella malinella, Caloptilia theivora, Phyllonorycter ringoniella, Phyllocnistis citrella, Acrolepiopsis sapporensis, Acrolepiopsis suzukiella, Plutella xylostella, Stathmopoda masinissa, Helcystogramma triannulella, Pectinophora gossypiella, Carposina sasakii, Cydla pomonella, Chilo suppressalis, Cnaphalocrocis medinalis, Conogethes punctiferalis, Diaphania indica, Etiella zinckenella, Glyphodes pyloalis, Hellula undalis, Ostrinia furnacalis, Ostrinia scapulalis, Ostrinia nubilalis, Parapediasia teterrella, Parnara guttata, Pieris brassicae, Pieris rapae crucivora, Ascotis selenaria, Pseudoplusia includens, Euproctis pseudoconspersa, Lymantria dispar, Orgyia thyellina, Hyphantria cunea, Lemyra imparilis, Adris tyrannus, Aedia leucomelas, Agrotis ipsilon, Agrotis segetum, Autographa nigrisigna, Ctenoplusia agnata, Helicoverpa armigera, Helicoverpa assulta, Helicoverpa zea, Heliothis virescens, Mamestra brassicae, Mythimna separata, Naranga aenescens, Spodoptera eridania, Spodoptera exigua, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Spodoptera depravata, Trichoplusia ni, Endopiza viteana, Manduca quinquemaculata and Manduca sexta;

Thysanoptera insects such as Frankliniella intonsa, Frankliniella occidentalis, Heliothrips haemorrhoidalis, Scirtothrips dorsalis, Thrips palmi, Thrips tabaci and Ponticulothrips diospyrosi;

Hemiptera insects such as Dolycoris baccarum, Eurydema rugosum, Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Glaucias subpunctatus, Halyomorpha halys, Nezara antennata, Nezara viridula, Piezodorus hybneri, Plautia crossota, Scotinophora lurida, Cletus punctiger, Leptocorisa chinensis, Riptortus clavatus, Rhopalus msculatus, Cavelerius saccharivorus, Togo hemipterus, Dysdercus cingulatus, Stephanitis pyrioides, Halticus insularis, Lygus lineolaris, Stenodema sibiricum, Stenotus rubrovittatus, Trigonotylus caelestialium, Arboridia apicalis, Balclutha saltuella, Epiacanthus stramineus, Empoasca fabae, Empoasca nipponica, Empoasca onukii, Empoasca sakaii, Macrosteles striifrons, Nephotettix cinctinceps, Psuedatomoscelis seriatus, Laodelphax striatella, Nilaparvata lugens, Sogatella furcifera, Diaphorina citri, Psylla pyrisuga, Aleurocanthus spiniferus, Bemisia argentifolii, Bemisia tabaci, Dialeurodes citri, Trialeurodes vaporariorum, Viteus vitifolii, Aphis gossypii, Aphis spiraecola, Myzus persicae, Toxoptera aurantii, Drosicha corpulenta, Icerya purchasi, Phenacoccus solani, Planococcus citri, Planococcus kuraunhiae, Pseudococcus comstocki, Ceroplastes ceriferus, Ceroplastes rubens, Aonidiella aurantii, Comstockaspis pemiciosa, Fiorinia theae, Pseudaonidia paeoniae, Pseudaulacaspis pentagona, Pseudaulacaspis prunicola, Unaspis euonymi, Unaspis yanonensis and Cimex lectularius;

Coleoptera insects such as Anomala cuprea, Anomala rufocuprea, Gametis jucunda, Heptophylla picea, Popillia japonica, Lepinotarsa decemlineata, Melanotus fortnumi, Melanotus tamsuyensis, Lasioderma serricome, Epuraea domina, Epilachna varivestis, Epilachna vigintioctopunctata, Tenebrio molitor, Tribolium castaneum, Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, Xylotrechus pyrrhoderus, Callosobruchus chinensis, Aulacophora femoralis, Chaetocnema concinna, Diabrotica undecimpunctata, Diabrotica virgifera, Diabrotica barberi, Oulema oryzae, Phyllotreta striolata, Psylliodes angusticollis, Rhynchites heros, Cylas formicarius, Anthonomus grandis, Echinocnemus squameus, Euscepes postfasciatus, Hypera postica, Lissohoptrus oryzophilus, Otiorhynchus sulcatus, Sitophilus granarius, Sitophilus zeamais, Sphenophorus venatus vestitus and Paederus fuscipes;

Diptera insects such as Asphondylia yushimai, Sitodiplosis mosellana, Bactrocera cucurbitae, Bactrocera dorsalis, Ceratitis capitata, Hydrellia griseola, Drosophila suzukii, Agromyza oryzae, Chromatomyia horticola, Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae, Liriomyza trifolii, Delia platura, Pegomya cunicularia, Rhagoletis pomonella, Mayetiola destructor, Musca domestica, Stomoxys calcitrans, Melophagus ovinus, Hypoderma bovis, Hypoderma lineatum, Oestrus ovis, Glossina palpalis (Glossina morsitans), Prosimulium yezoensis, Tabanus trigonus, Telmatoscopus albipunctatus, Leptoconops nipponensis, Culex pipiens pallens, Aedes aegypti, Aedes albopicutus and Anopheles hyracanus sinesis;

Hymenoptera insects such as Apethymus kuri, Athalia rosae, Arge pagana, Neodiprion sertifer, Dryocosmus kuriphilus, Eciton burchelli (Eciton schmitti), Camponotus japonicus, Vespa mandarina, Myrmecia spp., Solenopsis spp. and Monomorium pharaonis;

Orthoptera insects such as Teleogryllus emma, Gryllotalpa orientalis, Locusta migratoria, Oxya yezoensis and Schistocerca gregaria;

Collembolan insects such as Onychiurus folsomi, Onychiurus sibiricus and Bourletiella hortensis;

Dictyoptera insects such as Periplaneta fuliginosa, Periplaneta japonica and Blattella germanica;

Isoptera insects such as Coptotermes formosanus, Reticulitermes speratus and Odontotermes formosanus;

Siphonaptera insects such as Ctenocephalidae felis, Ctenocephalides canis, Echidnophaga gallinacea, Pulex irritans and Xenopsylla cheopis;

Mallophaga insects such as Menacanthus stramineus and Bovicola bovis;

Anoplura insects such as Haematopinus eurysternus, Haematopinus suis, Linognathus vituli and Solenopotes capillatus;

Tarsonemidae such as Phytonemus pallidus, Polyphagotarsonemus latus and Tarsonemus bilobatus;

Eupodidae such as Penthaleus erythrocephalus and Penthaleus major;

Tetranychidae such as Oligonychus shinkajii, Panonychus citri, Panonychus mori, Panonychus ulmi, Tetranychus kanzawai and Tetranychus urticae;

Eriophydae such as Acaphylla theavagrans, Aceria tulipae, Aculops lycopersici, Aculops pelekassi, Aculus schlechtendali, Eriophyes chibaensis and Phyllocoptruta oleivora;

Acaridae such as Rhizoglyphus robini, Tyrophagus putrescentiae and Tyrophagus similis;

Varroa destructor such as Varroa jacobsoni;

Ixodidae such as Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, Haemophysalis flava, Haemophysalis campanulata, Ixodes ovatus, Ixodes persulcatus, Amblyomma spp. and Dermacentor spp.

Cheyletidae such as Cheyletiella yasguri and Cheyletiella blakei;

Demodicidae such as Demodex canis and Demodex cati;

Psoroptidae such as Psoroptes ovis;

Sarcoptidae such as Sarcoptes scabiei, Notoedres cati and Knemidocoptes spp;

Crustacea such as Armadillidium vulgare;

Gastropoda such as Pomacea canaliculata, Achatina fulica, Meghimatium bilineatum, Limax Valentiana, Acusta despecta sieboldiana and Euhadra peliomphala; and

Nematoda such as Prathylenchus coffeae, Prathylenchus penetrans, Prathylenchus vulnus, Globodera rostochiensis, Heterodera glycines, Meloidogyne hapla, Meloidogyne incognita, Aphelenchoides besseyi and Bursaphelenchus xylophilus,

which should not be construed as limiting the scope of the present invention.

In addition, specific examples of the internal parasites of domestic animals, fowls, pet animals or the like capable of being controlled using the compound of the present invention include:

Nematoda such as Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia, Trichuris, Storongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris and Parascaris;

Nematoda, Filariidae such as Wuchereria, Brugia, Onchoceca, Dirofilaria and Loa;

Nematoda, Dracunculidae such as Deacunculus;

Cestoda such as Dipylidium caninum, Taenia taeniaeformis, Taenia solium, Taenia saginata, Hymenolepis diminuta, Moniezia benedeni, Diphyllobothrium latum, Diphyllobothrium erinacei, Echinococcus granulosus and Echinococcus multilocularis;

Trematoda such as Fasciola hepatica and F. gigantica, Paragonimus westermanii, Fasciolopsic bruski, Eurytrema pancreaticum and E. coelomaticum, Clonorchis sinensis, Schistosoma japonicum, Schistosoma haematobium and Schistosoma mansoni;

Eimeria spp. such as Eimeria tenella, Eimeria acervulina, Eimeria brunetti, Eimeria maxima, Eimeria necatrix, Eimeria bovis and Eimeria ovinoidalis;

Trypanosomsa cruzi; Leishmania spp.; Plasmodium spp.; Babesis spp.; Trichomonadidae spp.; Histomanas spp.; Giardia spp.; Toxoplasma spp.; Entamoeba histolytica and Theileria spp,

which should not be construed as limiting the scope of the present invention.

Furthermore, the compound of the present invention is effective against pests which have developed the resistance to the related art insecticides such as organic phosphorus-based compounds, carbamate-based compounds or pyrethroid-based compounds.

That is, the compound of the present invention can effectively control pests belonging to insects such as Collembola, Dictyoptera (Blattaria), Orthoptera, Isoptera, Thysanoptera, Hemiptera (Heteroptera and Homoptera), Lepidoptera, Coleoptera, Hymenoptera, Diptera, Isoptera (Siphonaptera) and Phthiraptera; mites; Gastropoda; and Nematoda with a low concentration. On the other hand, the compound of the present invention has an extremely useful characteristic of having substantially no adverse effect on mammals, fish, Crustacea and beneficial insects (useful insects such as Apidae and Bombus, and natural enemies such as Aphelinidae, Aphidiidae, Tachinidae, Orius and Amblyseius).

For using the compound of the present invention, the compound can be put to practical use as a preparation in any formulation such as a soluble concentrate, an emulsifiable concentrate, a wettable powder, a water soluble powder, a water dispersible granule, a water soluble granule, a suspension concentrate, a concentrated emulsion, a suspoemulsion, a microemulsion, a dustable powder, a granule, a tablet and an emulsifiable gel, typically by mixing the compound with an appropriate solid carrier or liquid carrier, further if desired by adding to the resultant mixture, a surfactant, a penetrant, a spreader, a thickener, an antifreezing agent, a binder, an anticaking agent, a disintegrant, an antifoamer, an antiseptic or a stabilizer. In addition, from the viewpoint of laborsaving and safety-enhancing, the compound can be put to use by encapsulating the above preparation in any formulation in a water soluble packaging material such as a water soluble capsule and a bag of water soluble film.

Examples of the solid carrier include: natural mineral matters such as quartz, calcite, sepiolite, dolomite, chalk, kaolinite, pyrophyllite, sericite, halloysite, methahalloysite, kibushi clay, gairome clay, pottery stone, zeeklite, allophane, Shirasu, mica, talc, bentonite, activated clay, acid clay, pumice, attapulgite, zeolite and diatom earth; burned products of natural mineral matters such as burned clay, perlite, Shirasu balloon, vermiculite, attapulgous clay and burned diatom earth; inorganic salts such as magnesium carbonate, calcium carbonate, sodium carbonate, sodium hydrogen carbonate, ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate and potassium chloride; saccharides such as glucose, fructose, sucrose and lactose; polysaccharides such as starch, powdered cellulose and dextrin; organic substances such as urea, urea derivatives, benzoic acid and salts of benzoic acid; plants such as wood flour, cork flour, corncob, walnut shell and tobacco stem; fly ash; white carbon (such as hydrous synthetic silica, anhydrous synthetic silica and hydrous synthetic silicate); and fertilizers.

Examples of the liquid carrier include: aromatic hydrocarbons such as xylene, alkyl (C₉, C₁₀, or the like) benzene, phenylxylylethane and alkyl (C₁, C₃, or the like) naphthalene; aliphatic hydrocarbons such as machine oil, n-paraffin, isoparaffin and naphthene; a mixture of aromatic hydrocarbons and aliphatic hydrocarbons such as kerosene; alcohols such as ethanol, isopropanol, cyclohexanol, phenoxyethanol and benzyl alcohol; polyalcohols such as ethylene glycol, propylene glycol, diethylene glycol, hexylene glycol, polyethylene glycol and polypropylene glycol; ethers such as propyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether and propylene glycol monophenyl ether; ketones such as acetophenone, cyclohexanone and γ-butyro lactone; esters such as aliphatic acid methyl esters, succinic acid dialkyl esters, glutamic acid dialkyl esters, dialkyl adipate esters, and dialkyl phthalate esters; acid amides such as N-alkyl (C₁, C₈, C₁₂, or the like) pyrrolidone; oils and fats such as soybean oil, linseed oil, rapeseed oil, coconut oil, cottonseed oil and castor oil; dimethyl sulfoxide; and water.

These solid or liquid carriers may be used individually or in combination of two or more types thereof.

Examples of the surfactant include: nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl (mono- or di-)phenyl ethers, polyoxyethylene (mono-, di- or tri-)stylyl phenyl ethers, polyoxyethylene-polyoxypropylene block copolymers, polyoxyethylene aliphatic acid (mono- or di-) esters, sorbitan aliphatic acid esters, polyoxyethylene sorbitan aliphatic acid esters, castor oil ethylene-oxide adducts, acetylene glycol, acetylene alcohols, acetylene glycol ethylene-oxide adducts, acetylene alcohol ethylene-oxide adducts and alkylglucosides; anionic surfactants such as alkyl sulfate ester salts, alkylbenzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkylnaphthalene sulfonates, salts of naphthalene sulfonate formalin condensate, salts of alkylnaphthalene sulfonate formalin condensate, polyoxyethylenealkylether sulfate or phosphate esters, polyoxyethylene (mono- or di-)alkylphenyl ether sulfate or phosphate esters, polyoxyethylene (mono-, di- or tri-)stylylphenyl ether sulfate or phosphate esters, polycarboxylic acid salts (such as polyacrylic acid salts, polymaleic acid salts and maleic acid-olefin copolymer) and polystylene sulfonates; cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts; amphoteric surfactants such as amino acid-type surfactants and betaine-type surfactants; silicone-based surfactants; and fluorinated surfactants.

Although the content of these surfactants is not particularly limited, it is desirably in a range of usually 0.05 to 20 parts by weight, relative to 100 parts by weight of the preparation of the present invention. In addition, these surfactants may be used individually or in combination of two or more types thereof.

Although the application dosage of the compound of the present invention varies depending on the application situation, the application period, the application method, the cultivated crop and the like, it is generally appropriate to be around 0.005 to 50 kg per hectare (ha) as an active ingredient amount.

On the other hand, in using the compound of the present invention for controlling external or internal parasites of mammals and birds as domestic animals and pet animals, an effective amount of the compound of the present invention can be administered together with additives for the preparation by: oral administration and parenteral administration such as injections (intramuscular, subcutaneous, intravenous and intraperitoneal injections); a percutaneous administration such as immersing, spraying, bathing, cleaning, pouring-on and spotting-on, and dusting; and transnasal administration. The compound of the present invention can be administered also as a molded product using a strip, a plate, a band, a collar, an ear mark, a limb band and an indicator. For the administration of the compound of the present invention, the compound can be prepared in any formulation suitable for an administration route.

Examples of the formulation in any form to be prepared include solid preparations such as dustable powders, granules, wettable powders, pellets, tablets, boluses, capsules and molded products containing activated compounds; soluble concentrates for injection, soluble concentrates for oral administration and soluble concentrates used on the skin or in the body cavity; solution preparations such as pour-on drugs, spot-on drugs, flowable drugs and emulsifiable concentrates; and semisolid preparations such as ointments and gels.

The solid preparation can be mainly used for oral administration, percutaneous administration of the preparation diluted with water, or an environmental treatment. The solid preparation can be prepared by mixing an activated compound with an appropriate excipient, if necessary together with an adjuvant, and converting the resultant mixture into a desired form. Examples of the appropriate excipient include: inorganic substances such as carbonate salts, hydrogen carbonate salts, phosphate salts, aluminum oxide, silica and clay; and organic substances such as saccharides, celluloses, ground grains and starch.

The soluble concentrate for injection can be prepared by dissolving an activated compound capable of being administered intravenously, intramuscularly or subcutaneously in an appropriate solvent, and if necessary by adding to the resultant solution, additives such as solubilizers, acids, bases, buffering salts, antioxidants and protective agents. Examples of the appropriate solvent include water, ethanol, butanol, benzyl alcohol, glycerin, propylene glycol, polyethylene glycol, N-methylpyrrolidone, mixtures thereof, physiologically acceptable vegetable oils and synthetic oils suitable for injection. Examples of the solubilizer include polyvinylpyrrolidone, polyoxyethylated castor oil and polyoxyethylated sorbitan esters. Examples of the protective agents include benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters and n-butanol.

The soluble concentrate for oral administration can be administered directly or as a diluted soluble concentrate and can be prepared in substantially the same manner as that in the case of the soluble concentrate for injection.

The flowable drug, the emulsifiable concentrate and the like can be administered percutaneously directly or as a diluted drug, or through an environmental treatment.

The soluble concentrate used on the skin can be administrated by dropping, spreading, rubbing, spraying, dusting or immersing (immersing, bathing or cleaning) to apply the drug on the skin. These soluble concentrates can be prepared in substantially the same manner as that in the case of the soluble concentrate for injection.

The pour-on drug and the spot-on drug are dropped or sprayed on a limited range of the skin, so that these drugs can immerse activated compounds thereof into the skin to obtain the systemic effect. The pour-on drug and the spot-on drug can be prepared by dissolving, suspending or emulsifying an active ingredient in an appropriate skin-adaptable solvent or solvent mixture. If necessary, in these drugs, an adjuvant such as a surfactant, a colorant, an absorption-accelerating substance, an antioxidant, a light stabilizer and an adhesive can be incorporated.

Examples of the appropriate solvent include water, alkanol, glycol, polyethylene glycol, polypropylene glycol, glycerin, benzyl alcohol, phenylethanol, phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate, dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, acetone, methyl ethyl ketone, aromatic and/or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, liquid paraffin, light liquid paraffin, silicone, dimethylacetoamide, N-methylpyrrolidone or 2,2-dimethyl-4-oxy-methylene-1,3-dioxolane. Examples of the absorption accelerating substance include DMSO, isopropyl myristate, dipropylene glycol pelargonate, silicone oil, aliphatic esters, triglycerides and aliphatic alcohols. Examples of the antioxidant include sulfites, metabisulfites, ascorbic acid, butylhydroxytoluene, butylated hydroxyanisole and tocopherol.

The emulsifiable concentrate can be administered by an oral administration, a percutaneous administration or an injection. The emulsifiable concentrate can be prepared by dissolving an active ingredient in a hydrophobic phase or a hydrophilic phase and homogenizing the resultant solution with a solvent of another type of phase using an appropriate emulsifier, if necessary further together with an adjuvant such as a colorant, an absorption accelerating substance, a protective agent, an antioxidant, a sunscreen and a thickener substance.

Examples of the hydrophobic phase (oil) include paraffin oil, silicone oil, sesame oil, almond oil, castor oil, synthetic triglyceride, ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol pelargonate, an ester of a branched aliphatic acid having a short chain length with a saturated aliphatic acid having a chain length of C16 to C18, isopropyl myristate, isopropyl palmitate, caprylate/caprate esters of a saturated aliphatic alcohol having a chain length of C12 to C18, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, a wax-like aliphatic acid ester, dibutyl phthalate, diisopropyl adipate, isotridecyl alcohol, 2-octyl dodecanol, cetylstearyl alcohol and oleyl alcohol.

Examples of the hydrophilic phase include water, propylene glycol, glycerin and sorbitol.

Examples of the emulsifier include: nonionic surfactants such as polyoxyethylated castor oil, polyoxyethylated monoolefin acid sorbitan, sorbitan monostearate, glycerin monostearate, polyoxyethyl stearate and alkylphenol polyglycol ether; amphoteric surfactants such as disodium N-lauryl-β-iminodipropionate and lecithin; anionic surfactants such as sodium laurylsulfate, aliphatic alcohol sulfate ether and mono-/di-alkyl polyglycol orthophosphate ester monoethanolamine salt; and cationic surfactants such as cetyltrimethylammonium chloride.

Examples of the other adjuvants include carboxymethyl cellulose, methyl cellulose, polyacrylate, alginate, gelatin, gum Arabic, polyvinylpyrrolidone, polyvinyl alcohol, methyl vinyl ether, copolymers of maleic anhydride, polyethylene glycol, wax and colloidal silica.

The semisolid preparation can be administered by applying or spreading the preparation on the skin or by introducing the preparation into a body cavity. The gel can be prepared by adding to a solution prepared as described above with respect to the soluble concentrate for injection, a thickener in an amount sufficient for generating an ointment-like transparent substance having viscosity.

Next, examples of the formulation of the preparation in the case of using the compound of the present invention are described, with the proviso that the formulation examples of the present invention are not limited to these examples. Here, in the following formulation examples, the term “part” represents a part by weight.

(Wettable powder) Compound of the present invention 0.1 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 part(s) Others 0 to 5 parts

Other examples include an anticaking agent and a stabilizer.

(Emulsifiable concentrate) Compound of the present invention 0.1 to 30 parts Liquid carrier 45 to 95 parts Surfactant 4.9 to 15 parts Others 0 to 10 parts

Other examples include a spreader and a stabilizer.

(Suspension concentrate) Compound of the present invention 0.1 to 70 parts Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 part(s) Others 0.01 to 30 parts

Other examples include an antifreezing agent and a thickener.

(Water dispersible granule) Compound of the present invention 0.1 to 90 parts Solid carrier 0 to 98.9 parts Surfactant 1 to 20 part(s) Others 0 to 10 parts

Other examples include a binder and a stabilizer.

(Soluble concentrate) Compound of the present invention 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0 to 10 parts

Other examples include an antifreezing agent and a spreader.

(Granule) Compound of the present invention 0.01 to 80 parts Solid carrier 10 to 99.99 parts Others 0 to 10 parts

Other examples include a binder and a stabilizer.

(Dustable powder) Compound of the present invention 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0 to 5 parts

Other examples include an antidrift agent and a stabilizer.

Next, examples of the preparation containing the compound of the present invention as an active ingredient are more specifically described, however the examples should not be construed as limiting the scope of the present invention.

Here, in the following formulation examples, the term “parts” represents parts by weight.

(Formulation example 1) Wettable powder prepared by homogeneously mixing and grinding a composition containing: compound of the present invention No. 1-003 20 parts; pyrophyllite 74 parts; SORPOL 5039  4 parts (trade name; manufactured by TOHO Chemical Industry Co., LTD.; mixture of nonionic surfactant and anionic surfactant); and CARPLEX #80D  2 parts (trade name; manufactured by Shionogi & Co., Ltd.; synthetic hydrous silicic acid).

(Formulation example 2) Emulsifiable concentrate prepared by homogeneously mixing a composition containing: compound of the present invention No. 1-003  5 parts; xylene 75 parts; N-methylpyrrolidone 15 parts; and SORPOL 2680  5 parts (trade name; manufactured by TOHO Chemical Industry Co., LTD.; mixture of nonionic surfactant and anionic surfactant).

(Formulation example 3) Suspension concentrate prepared by homogeneously mixing a composition containing: compound of the present invention No. 1-003   25 parts; AGRISOL S-710   10 parts (trade name; manufactured by Kao Corporation; nonionic surfactant); LUNOX 1000C  0.5 parts (trade name; manufactured by TOHO Chemical Industry Co., LTD.; anionic surfactant); xanthan gum  0.2 parts; and water 64.3 parts, and then wet-grinding the resultant mixture.

(Formulation example 4) Water dispersible granule prepared by homogeneously mixing and grinding a composition containing: compound of the present invention No. 1-003 75 parts; HITENOL NE-15  5 parts; (trade name; manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.; anionic surfactant); VANILLEX N 10 parts (trade name; manufactured by Nippon Paper Industries Co., Ltd.; anionic surfactant); and CARPLEX #80D 10 parts (trade name; manufactured by Shionogi & Co., Ltd.; synthetic hydrous silicic acid), then adding a small amount of water to the resultant mixture to stir and mix the mixture, granulating the mixture with an extrusion granulator, and drying the resultant granules.

(Formulation example 5) Granule prepared by homogeneously mixing and grinding a composition containing: compound of the present invention No. 1-003  5 parts; bentonite 50 parts; and talc 45 parts, then adding a small amount of water to the resultant mixture to stir and mix the mixture, granulating the mixture with an extrusion granulator, and drying the resultant granules.

(Formulation example 6) Dustable powder prepared by homogeneously mixing and grinding a composition containing: compound of the present invention No. 1-003   3 parts; CARPLEX #80D 0.5 parts (trade name; manufactured by Shionogi & Co., Ltd.; synthetic hydrous silicic acid); kaolinite 95 parts; and diisopropyl phosphate 1.5 parts.

For using the preparation, the preparation is diluted with water by 1 to 10,000 time(s) to be directly dusted or is directly dusted without dilution.

(Formulation example 7) Wettable powder preparation compound of the present invention No. 1-003 25 parts sodium diisobutylnaphthalenesulfonate 1 part calcium n-dodecylbenzenesulfonate 10 parts alkylaryl polyglycol ether 12 parts sodium salt of naphthalenesulfonic acid formalin condensate 3 parts emulsion-type silicone 1 part silicon dioxide 3 parts kaolin 45 parts

(Formulation example 8) Water soluble thickener preparation compound of the present invention No. 1-003 20 parts polyoxyethylene lauryl ether  3 parts sodium dioctylsulfosuccinate 3.5 parts  dimethylsulfoxide 37 parts 2-propanol 36.5 parts  

(Formulation example 9) Soluble concentrate for spraying compound of the present invention No. 1-003  2 parts dimethylsulfoxide 10 parts 2-propanol 35 parts acetone 53 parts

(Formulation example 10) Soluble concentrate for percutaneous administration compound of the present invention No. 1-003  5 parts hexylene glycol 50 parts isopropanol 45 parts

(Formulation example 11) Soluble concentrate for percutaneous administration compound of the present invention No. 1-003  5 parts propylene glycol monomethyl ether 50 parts dipropylene glycol 45 parts

(Formulation example 12) Soluble concentrate for percutaneous administration (dropping) compound of the present invention No. 1-003  2 parts light liquid paraffin 98 parts

(Formulation example 13) Soluble concentrate for percutaneous administration (dropping) compound of the present invention No. 1-003  2 parts light liquid paraffin 58 parts olive oil 30 parts ODO-H  9 parts Shin-Etsu silicone  1 part

In addition, when the compound of the present invention is used as an agricultural chemical, if necessary the compound may be mixed with another type of herbicide, various insecticides, a miticide, a nematicide, a fungicide, a plant growth regulator, a synergist, a fertilizer or a soil conditioner to be applied during the preparation or the dusting.

Particularly, by mixing the compound with other agricultural chemicals or phytohormones to be applied, a cost reduction by reducing the application dose, an enlargement of the insecticidal spectrum by a synergism of a mixed drug and a higher pest control effect can be expected. In this case, it is possible to combine simultaneously a plurality of publicly-known agricultural chemicals. Examples of types of agricultural chemicals to be mixed with the compound of the present invention to be used include compounds described in “The Pesticide Manual, vol. 14 (2006)”. Specific examples of the general names include the following names, to which the examples are not limited.

Fungicides: acibenzolar-S-methyl, acylaminobenzamide, acypetacs, aldimorph, amisulbrom, amobam, ampropylos, anilazine, azaconazole, azithiram, azoxystrobin, barium polysulfide, benalaxyl, benodanil, benomyl, benquinox, bentaluron, benthiavalicarb, benthiazole, benzamacril, benzamorf, bethoxazine, binapacryl, biphenyl, bitertanol, blasticidin-S, bordeaux mixture, boscalid, bromoconazole, bupirimate, buthiobate, calcium polysulfide, captafol, captan, carpropamid, carbamorph, carbendazim, carboxin, carvone, cheshunt mixture, chinomethionat, chlobenthiazone, chloraniformethane, chloranil, chlorfenazol, chloroneb, chloropicrin, chlorothalonil, chloroquinox, chlozolinate, climbazole, clotrimazole, copper acetate, copper carbonate basic, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper sulfate, copper sulfate basic, copper zinc chromate, cufraneb, cuprobam, cyazofamid, cyclafuramid, cycloheximide, cyflufenamid, cymoxanil, cypendazole, cyproconazol, cyprodinil, cyprofuram, dazomet, debacarb, decafentin, dehydroacetic acid, dichlofluanid, dichlone, dichlorophen, dichlozoline, dichlobutrazol, diclocymet, diclomedine, dicloran, diethofencarb, difenoconazole, diflumetorim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton, dinocap, dinocap-4, dinocap-6, dinocton, dinosulfon, dinoterbon, diphenylamine, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon, edifenphos, epoxiconazole, etaconazole, etem, ethirimol, ethoxyquin, etridiazole, famoxadone, fenarimol, febuconazole, fenamidone, fenaminosulf, fenapanil, fendazosulam, fenfuram, fenhexamid, fenitropan, fenoxanil, fenpiclonil, fenpropidin, fenpropimorph, fentin, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, flumorph, fluopicolide, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminium, fuberidazole, furalaxyl, furametpyr, furcarbanil, furconazole, fluconazole-cis, furmecyclox, furphanate, glyodin, griseofulvin, guazatine, halacrinate, hexachlorobenzene, hexaconazole, hexylthiofos, 8-hydroxyquinoline sulfate, hymexazol, imazalil, imibenconazole, iminoctadine, ipconazole, iprobenfos, iprodione, iprovalicarb, isoprothiolane, isovaledione, kasugamycin, kresoxim-methyl, mancopper, mancozeb, mandipropamid, maneb, mebenil, mecarbinzid, mepanipyrim, mepronil, metalaxyl, metalaxyl-M, metam, metazoxolon, metconazole, methasulfocarb, methfuroxam, methyl isothiocyanate, metiram, metominostrobin, metrafenone, metsulfovax, milneb, myclobutanil, myclozolin, nabam, natamycin, nickel bis(dimethyldithiocarbamate), nitrostyrene, nitrothal-isopropyl, nuarimol, OCH, octhilinone, ofurace, orysastrobin, oxadixyl, oxine copper, oxycarboxin, oxpoconazole fumarate, pefurzoate, penconazole, pencycuron, penthiopyrad, o-phenylphenol, phosdiphen, phthalide, picoxystrobin, piperalin, polycarbamate, polyoxins, polyoxorim, potassium azide, potassium hydrogen carbonate, proquinazid, probenazole, prochloraz, procymidone, propamocarb hydrochloride, propiconazole, propineb, prothiocarb, prothioconazole, pyracarbolid, pyraclostrobin, pyrazophos, pyridinitril, pyrifenox, pyrimethanil, pyroquilon, pyroxychlor, pyroxyfur, quinomethionate, quinoxyfen, quintozene, quinacetol-sulfate, quinazamid, quinconazole, rabenzazole, sodium azide, sodium hydrogen carbonate, sodium hypochlorite, sulfur, spiroxamine, salycylanilide, silthiofam, simeconazole, tebuconazole, tecnazene, tecoram, tetraconazole, thiabendazole, thiadifluor, thicyofen, thifluzamide, thiochlorfenphim, thiophanate, thiophanate-methyl, thioquinox, thiram, tiadinil, tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, toriadimenol, triamiphos, triarimol, triazoxide, triazbutil, tributyltin oxide, trichlamide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, vinclozolin, zarilamide, zinc sulfate, zineb, ziram, zoxamide, siitake mushroom mycelia extract, and the like.

Bactericides: benzalkonium chloride, bithionol, bronopol, cresol, formaldehyde, nitrapyrin, oxolinic acid, oxyterracycline, streptomycin, tecloftalam, and the like.

Nematicides: aldoxycarb, cadusafos, DBCP, dichlofenthion, DSP, ethoprophos, fenamiphos, fensulfothion, fosthiazate, fosthietan, imicyafos, isamidofos, isazofos, oxamyl, thionazin, and the like.

Miticides: acequinocyl, acrinathrin, amitraz, BCI-033 (test name), bifenazate, bromopropylate, chinomethionat, chlorobenzilate, clofentezine, cyenopyrafen, cyflumetofen, cyhexatine, dicofol, dienochlor, DNOC, etoxazole, fenazaquin, fenbutatin oxide, fenothiocarb, fenpropathrin, fenpyroximate, fluacrypyrim, halfenprox, hexythiazox, milbemectin, propargite, pyridaben, pyrimidifen, S-1870 (test name), spirodiclofen, spyromesifen, tebufenpyrad, and the like.

Insecticides: abamectin, acephate, acetamipirid, alanycarb, aldicarb, allethrin, azinphos-methyl, bacillus thuringiensis, bendiocarb, benfuracarb, bensultap, bifenthrin, buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, cartap, chlorantraniliprole, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chlromafenozide, clothianidin, cycloprothrin, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, diacloden, diafenthiuron, diazinon, dichlorvos, diflubenzuron, dimethylvinphos, dinotefuran, diofenolan, disulfoton, dimethoate, emamectin-benzoate, EPN, esfenvalerate, ethiofencarb, ethiprole, etofenprox, etrimfos, fenitrothion, fenobucarb, fenoxycarb, fenpropathrin, fenthion, fenvalerate, fipronil, flonicamid, flubendiamide, flucythrinate, flufenerim, flufenoxuron, flufenprox, fluvalinate, tau-fluvalinate, fonophos, formetanate, formothion, furathiocarb, halofenozide, hexaflumuron, hydramethylnon, imidacloprid, isofenphos, indoxacarb, isoprocarb, isoxathion, lepimectin, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methacrifos, metaflumizone, metalcarb, methomyl, methoprene, methoxychlor, methoxyfenozide, methyl bromide, monocrotophos, muscalure, nitenpyram, novaluron, omethoate, oxamyl, oxydemeton-methyl, oxydeprofos, parathion, parathion-methyl, pentachlorophenol (PCP), permethrin, phenthoate, phoxim, phorate, phosalone, phosmet, phosphamidon, pirimicarb, pirimiphos-methyl, profenofos, prothiofos, propaphos, protrifenbute, pymetrozine, pyraclofos, pyridalyl, pyrifluquinazon, pyriproxyfen, rotenone, SI-0405 (test name), sulprofos, silafluofen, spinetoram, spinosad, spirotetramat, sulfotep, SYJ-159 (test name), tebfenozide, teflubenzuron, tefluthorin, terbufos, tetrachlorvinphos, thiacloprid, thiocyclam, thiodicarb, thiamethoxam, thiofanox, thiometon, tolfenpyrad, tralomethrin, trichlorfon, triazuron, triflumuron, vamidothion, and the like.

EXAMPLES

Hereinafter, the present invention is described more in detail referring specifically to Synthetic Examples and Test Examples of the compound of the present invention as Examples, which should not be construed as limiting the scope of the present invention.

Synthetic Examples Synthetic Example 1

4-(4-bromo-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide (compound of the present invention No. 1-003 in the following Table 7).

Process 1; Production of methyl 4-(1Z,2Z)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-1-(hydroxyimino)-2-butenyl)-2-methyl benzoate (compound of the present invention No. 9-009 in the following Table 15)

In a nitrogen atmosphere, into a solution of 0.43 g of methyl 4-(5-3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl benzoate (compound No. 11-054 in Patent Document 1) in 10 mL of tetrahydrofuran, 1.0 mL of a 1.0 M lithium hexamethyldisilazane tetrahydrofuran solution was dropped at room temperature with stirring and after the completion of the dropping, the resultant mixture was continuously stirred at the same temperature further for 10 minutes. After the completion of the reaction, the reaction mixture was charged into 5 mL of ice water and thereto, a 2N hydrochloric acid aqueous solution was added, followed by extracting the resultant reaction mixture with ethyl acetate (20 mL×1) under an acidic condition. The organic phase was washed with water and then dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off from the organic phase under reduced pressure, followed by purifying the resultant residue by silica gel column chromatography eluting with ethyl acetate-hexane (2:3) to obtain 0.40 g of the objective substance as a light yellow resinoid.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.34 (s, 1H), 7.95 (d, J=10.8 Hz, 1H), 7.4-7.5 (m, 5H), 6.79 (s, 1H), 3.92 (s, 3H), 2.64 (s, 3H).

Process 2; Production of methyl 4-(4-bromo-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl benzoate (compound of the present invention No. 4-005 in the following Table 10)

To a solution of 0.56 g of methyl 4-((1Z,2Z)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-1-(hydroxyimino)-2-butenyl)-2-methyl benzoate in 10 mL of benzene, 0.25 g of N-bromosuccinimide was added and the resultant mixture was stirred at room temperature for 16 hours. After the completion of the reaction, the insoluble substance was filtered off and the solvent was distilled off under reduced pressure, followed by purifying the resultant residue by silica gel column chromatography eluting with ethyl acetate to obtain 0.38 g of the objective substance as a white crystal.

Melting point: 183.0 to 185.5° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.01 (d, J=10.8 Hz, 1H), 7.65-7.75 (m, 2H), 7.45-7.6 (m, 3H), 5.88 (s, 1H), 3.93 (s, 3H), 2.67 (s, 3H)

Process 3; Production of 4-(4-bromo-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl benzoic acid

To a solution of 0.38 g of methyl 4-(4-bromo-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl benzoate in 10 mL of methanol, a solution of 0.25 g of potassium hydroxide in 5 mL of water was added and the resultant mixture was stirred while heating the mixture to reflux for 2 hours. After the completion of the reaction, methanol was distilled off under reduced pressure and to the residual aqueous solution, a 2N hydrochloric acid aqueous solution was added to acidize the aqueous solution, followed by extracting the aqueous solution with ethyl acetate (20 mL×2). The organic phase was dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off from the organic phase under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:1) to obtain 0.15 g of the objective substance as a colorless resinoid.

Process 4; Production of 4-(4-bromo-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide

To a solution of 0.15 g of 4-(4-bromo-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl benzoic acid, 0.06 g of 2,2,2-trifluoroethylamine and 0.09 g of triethylamine in 4 mL of dichloromethane, 0.11 g of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride was added and the resultant mixture was stirred at room temperature for 15 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:1) to obtain 0.03 g of the objective substance as a light yellow resinoid.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.6-7.75 (m, 2H), 7.4-7.6 (m, 4H), 6.15-6.25 (m, 1H), 5.88 (s, 1H), 4.05-4.2 (m, 2H), 2.48 (s, 3H).

Synthetic Example 2

4-(5-(3,5-dichlorophenyl)-4-methylthio-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide (compound of the present invention No. 1-005 in the following Table 7)

Process 1; Production of methyl 4-(5-(3,5-dichlorophenyl)-4-methylthio-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl benzoate

To a solution of 0.30 g of methyl 4-(4-bromo-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl benzoate synthesized in Process 2 of Synthetic Example 1 in 6 mL of N,N-dimethylformamide, a suspension of 0.04 g of sodium thiomethoxide in 1 mL of N,N-dimethylformamide was added while ice-cooling and stirring the solution and the resultant mixture was stirred at the same temperature for 2 hours. After the completion of the reaction, the reaction mixture was charged into 3 mL of ice water and the resultant reaction mixture was extracted with ethyl acetate (10 mL×2). The organic phase was washed with 5 mL of a 2N hydrochloric acid aqueous solution and then dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off from the organic phase under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:9) to obtain 0.08 g of the objective substance as a colorless resinoid.

Process 2; Production of 4-(5-(3,5-dichlorophenyl)-4-methylthio-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl benzoic acid

Methyl 4-(5-(3,5-dichlorophenyl)-4-methylthio-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl benzoate was dissolved in 10 mL of ethanol, and to the resultant solution, a solution of 5 mL of an aqueous solution containing 0.06 g of potassium hydroxide was added, followed by stirring the resultant mixture at 70° C. for 1 hour. After the completion of the reaction, ethanol was distilled off under reduced pressure and to the resultant residue, 5 mL of water was added. The resultant reaction mixture was washed with 5 mL of diethyl ether and thereto, a 2N hydrochloric acid aqueous solution was added to acidize the reaction mixture, followed by extracting the resultant reaction mixture with diethyl ether (5 mL×2). The organic phase was dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order, and then the solvent was distilled off from the organic phase under reduced pressure, followed by purifying the resultant residue by silica gel column chromatography eluting with ethyl acetate-hexane (1:1) to obtain 0.06 g of the objective substance as a colorless resinoid.

Process 3; Production of 4-(5-(3,5-dichlorophenyl)-4-methylthio-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide

4-(5-(3,5-dichlorophenyl)-4-methylthio-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl benzoic acid was dissolved in 3 mL of dichloromethane, and to the resultant solution, 0.01 g of 2,2,2-trifluoroethylamine, 0.01 g of triethylamine and 0.03 g of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride were added, followed by stirring the resultant mixture at room temperature for 20 hours. After the completion of the reaction, to the reaction mixture, 6 mL of water was added and the resultant reaction mixture was extracted with ethyl acetate (10 mL×2). The organic phase was dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order, and then the solvent was distilled off from the organic phase under reduced pressure, followed by purifying the resultant residue by silica gel column chromatography eluting with ethyl acetate-hexane (1:1) to obtain 0.01 g of the objective substance as a colorless resinoid.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.7-7.85 (m, 2H), 7.56 (s, 2H), 7.4-7.5 (m, 2H), 6.0-6.15 (m, 1H), 4.96 (s, 1H), 4.05-4.2 (m, 2H), 2.50 (s, 3H), 1.43 (s, 3H).

Synthetic Example 3

4-(5-(3,5-dichlorophenyl)-4-methyl-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide (compound of the present invention No. 1-004 in the following Table 7).

Process 1; Production of methyl 4-(5-(3,5-dichlorophenyl)-4-methyl-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl benzoate

In a nitrogen atmosphere, into a solution of 1.30 g of methyl 4-(5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl benzoate (compound No. 11-054 in Patent Document 1) in 30 mL of tetrahydrofuran, 3.30 mL of a 1.0 M lithium hexamethyldisilazane tetrahydrofuran solution was dropped at −78° C. with stirring and after the completion of the dropping, the resultant mixture was continuously stirred at the same temperature further for 30 minutes. Next, to the reaction mixture, 4.26 g of methyl iodide was added and the resultant reaction mixture was heated to room temperature while continuing the stirring of the reaction mixture further for 1 hour. After the completion of the reaction, the reaction mixture was charged into 30 mL of ice water and thereto, a 2N hydrochloric acid aqueous solution was added, followed by extracting the resultant reaction mixture with ethyl acetate (50 mL×2) under an acidic condition. The organic phase was washed with water and then dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off from the organic phase under reduced pressure, followed by purifying the resultant residue by silica gel column chromatography eluting with ethyl acetate-hexane (1:4) to obtain 1.65 g of the objective substance as a light yellow resinoid.

Process 2; Production of 4-(5-(3,5-dichlorophenyl)-4-methyl-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl benzoic acid

To a solution of 1.65 g of methyl 4-(5-(3,5-dichlorophenyl)-4-methyl-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl benzoate in 60 mL of ethanol, a solution of 1.04 g of potassium hydroxide in 30 mL of water was added and the resultant mixture was stirred while heating the mixture to reflux for 6 hours. After the completion of the reaction, ethanol was distilled off under reduced pressure and to the residual aqueous solution, a 2N hydrochloric acid aqueous solution was added to acidize the aqueous solution, followed by extracting the aqueous solution with ethyl acetate (40 mL×2). The organic phase was dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off from the organic phase under reduced pressure to obtain 0.30 g of a crude objective substance as a light yellow solid.

Process 3; Production of 4-(5-(3,5-dichlorophenyl)-4-methyl-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide

To a solution of 0.30 g of crude 4-(5-(3,5-dichlorophenyl)-4-methyl-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl benzoic acid, 0.14 g of 2,2,2-trifluoroethylamine and 0.21 g of triethylamine in 10 mL of dichloromethane, 0.27 g of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride was added and the resultant mixture was stirred at room temperature for 22 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (3:7) to obtain 0.07 g of the objective substance as a light yellow resinoid.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.4-7.6 (m, 6H), 6.15-6.25 (m, 1H), 4.05-4.25 (m, 3H), 2.46 (m, 3H), 0.93 (d, J=10.0 Hz, 3H).

Synthetic Example 4

4-(4-chloro-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide (compound of the present invention No. 1-002 in the following Table 7).

Process 1; Production of methyl 4-(4-chloro-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl benzoate

In a nitrogen atmosphere, into a solution of 2.00 g of methyl 4-(5-3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl benzoate (compound No. 11-054 in Patent Document 1) in 30 mL of tetrahydrofuran, 7.40 mL of a 1.0 M lithium hexamethyldisilazane tetrahydrofuran solution was dropped at −78° C. with stirring and thereto, 4.95 g of N-chlorosuccinimide was added, followed by continuing the stirring of the resultant mixture at the same temperature for 4 hours. After the completion of the reaction, the reaction mixture was charged into 50 mL of water and the resultant reaction mixture was extracted with ethyl acetate (40 mL×2). The organic phase was washed with water and then dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off from the organic phase under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:5) to obtain 0.12 g of the objective substance as a light yellow resinoid.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.00 and 7.96 (d, J=8.1 Hz, 1H), 7.45-7.75 (m, 5H), 5.87 and 5.68 (s, 1H), 3.93 and 3.91 (s, 3H), 2.66, 2.63 (s, 3H).

Process 2; Production of 4-(4-chloro-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide

To a solution of 0.12 g of methyl 4-(4-chloro-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl benzoate in 10 mL of methanol, a solution of 0.20 g of potassium hydroxide in 5 mL of water was added and the resultant mixture was stirred at 90° C. for 6 hours. After the completion of the reaction, to the reaction mixture, 5 mL of concentrated hydrochloric acid was added to acidize the reaction mixture and then the reaction mixture was extracted with ethyl acetate (30 mL×2). The organic phase was dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off from the organic phase under reduced pressure. The resultant residue was dissolved in 10 mL of dichloromethane, and to the resultant solution, 0.10 g of oxalyl chloride and 0.05 mL of N,N-dimethylformamide were added, followed by stirring the resultant mixture at room temperature for 1 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure and the resultant residue was dissolved in 10 mL of dichloromethane. To the resultant solution, 0.10 g of 2,2,2-trifluoroethylamine and 0.20 g of triethylamine were added and the resultant mixture was stirred at room temperature for 1 hour. After the completion of the reaction, to the reaction mixture, 20 mL of ethyl acetate was added and an insoluble substance was filtered off, followed by distilling off the solvent under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:2) to obtain 0.06 g of the objective substance as a white crystal.

Melting point: 127.0 to 128.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.4-7.75 (m, 6H), 6.14 (bs, 1H), 5.87 (s, 1H), 3.9-4.2 (m, 2H), 2.49 (s, 3H).

Synthetic Example 5

4-(4-bromo-5-(3,5-bis(trifluoromethyl)phenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl) benzoic acid amide (compound of the present invention No. 1-001 in the following Table 7).

To a solution of 0.55 g of 4-(4-bromo-5-(3,5-bis(trifluoromethyl)phenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl) benzoic acid synthesized in substantially the same manner as in Processes 1 to 3 of Synthetic Example 1 in 10 mL of dichloromethane, 0.15 g of oxalyl chloride and 2 drops of N,N-dimethylformamide were added and the resultant mixture was stirred at room temperature for 20 minutes. After the completion of the reaction, the solvent was distilled off under reduced pressure and the resultant residue was dissolved in 1 mL of tetrahydrofuran, followed by dropping the resultant solution into a mixture of 2 mL of concentrated ammonia water and 2 mL of tetrahydrofuran with stirring at room temperature. After the completion of the dropping, the resultant reaction mixture was continuously stirred at the same temperature further for 10 minutes. After the completion of the reaction, to the reaction mixture, 5 mL of water was added and the resultant reaction mixture was extracted with ethyl acetate (10 mL×1). The organic phase was washed with 5 mL of a 2N hydrochloric acid aqueous solution and dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off from the organic phase under reduced pressure. To the resultant residue, 2 mL of a solvent mixture of ethyl acetate-hexane (1:1) was added and the resultant mixture was stirred at room temperature for 30 minutes, followed by filtering a separated-out crystal to obtain 0.53 g of the objective substance as a white crystal.

Melting point: 190.0 to 193.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.07 (bs, 1H), 8.01 (s, 1H), 7.93 (s, 5H), 5.98 (s, 1H).

Synthetic Example 6

4-(4-bromo-5-(3,5-bis(trifluoromethyl)phenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-N-(methoxyiminomethyl)benzoic acid amide (compound of the present invention No. 1-011 in the following Table 7).

A solution of 0.12 g of 4-(4-bromo-5-(3,5-bis(trifluoromethyl)phenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl) benzoic acid amide synthesized in Synthetic Example 5 and 0.05 g of N,N-dimethylformamide dimethylacetal in 2 mL of tetrahydrofuran was stirred at room temperature for 15 hours. Next, to the reaction mixture, a solution of 0.04 g of methoxyamine hydrochloride in 2 mL of water was added and the resultant mixture was continuously stirred at room temperature further for 10 minutes. After the completion of the reaction, to the reaction mixture, 5 mL of water was added and the resultant mixture was extracted with ethyl acetate (10 mL×1). The organic phase was dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off from the organic phase under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:1) to obtain 0.10 g of the objective substance as a white crystal.

Melting point: 118.0 to 122.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.88 and 8.63 (d, J=9.6 Hz, 1H), 7.85-8.2 (m, 6H), 7.82 (d, J=9.9 Hz, 1H), 5.98 and 5.30 (s, 1H), 3.95 and 3.82 (s, 3H).

Synthetic Example 7

4-((2Z)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-1-(hydroxyimino)-2-butenyl)-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide (compound of the present invention No. 5-001 in the following Table 11).

In a nitrogen atmosphere, into a solution of 0.20 g of 4-(5-3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide (compound No. 5-075 in Patent Document 1) in 4 mL of tetrahydrofuran, 0.8 mL of a 1.0 M lithium hexamethyldisilazane tetrahydrofuran solution was dropped at room temperature with stirring. The resultant mixture was stirred at room temperature for 3 minutes and the reaction mixture was charged into 3 mL of ice water, and thereto, a 2N hydrochloric acid aqueous solution was added and the resultant reaction mixture was extracted with diethyl ether (10 mL×2) under an acidic condition. The organic phase was washed with water and then dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order, followed by distilling off the solvent from the organic phase under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (3:7) to obtain 0.12 g of the objective substance as a white crystal.

Melting point: 133.0 to 135.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.97 (s, 1H), 7.4-7.55 (m, 6H), 6.76 (s, 1H), 6.0-6.1 (m, 1H), 4.05-4.2 (m, 2H), 2.48 (s, 3H).

Synthetic Example 8

4-((2E)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-1-(hydroxyimino)-2-butenyl)-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide (compound of the present invention No. 6-001 in the following Table 12).

In a nitrogen atmosphere, into a solution of 0.75 g of 4-(5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide (compound No. 5-075 in Patent Document 1) in 20 mL of tetrahydrofuran, 2.24 mL of a 1.0 M lithium hexamethyldisilazane tetrahydrofuran solution was dropped at room temperature with stirring. The resultant mixture was stirred at room temperature for 1 hour and into the mixture, 3.0 mL of a 1.0 M lithium hexamethyldisilazane tetrahydrofuran solution was further dropped. After the completion of the dropping, the resultant mixture was continuously stirred at the same temperature further for 30 minutes. After the completion of the reaction, the reaction mixture was charged into 20 mL of ice water and thereto, a 2N hydrochloric acid aqueous solution was added, followed by extracting the resultant reaction mixture with ethyl acetate (40 mL×2) under an acidic condition. The organic phase was washed with water and then dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off from the organic phase under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:1) to obtain 0.26 g of the objective substance as a colorless resinoid.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 9.77 (s, 1H), 7.39 (s, 1H), 6.9-7.25 (m, 6H), 6.25 (t, J=8.4 Hz, 1H), 3.95-4.2 (m, 2H), 2.44 (s, 3H).

Synthetic Example 9

Tert-butyl N-(2-bromo-4-((2Z)-3-(3,5-dichlorophenyl)-1-hydroxyimino-4,4,4-trifluoro-2-butenyl)phenylmethyl)-N-(cyclopropylcarbonyl) carbamate (compound of the present invention No. 7-004 in the following Table 13).

Process 1; Production of 3-bromo-4-methylbenzaldoxime

To a solution of 17.9 g of 3-bromo-4-methylbenzaldehyde in 150 mL of methanol and 100 mL of water, 7.6 g of hydroxylamine hydrochloride was added and the resultant mixture was stirred at 70° C. for 3 hours. After the completion of the reaction, the reaction mixture was left to be cooled down to room temperature and was diluted with 150 mL of ethyl acetate to be washed with water (100 mL×1). Further, the reaction mixture was dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order and the solvent was distilled off under reduced pressure to obtain 19.1 g of the objective substance as a brown crystal. This crystal was used in the next process without being further purified.

Melting point: 55.0 to 59.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.06 (s, 1H), 7.74 (s, 1H), 7.39 (d, J=7.5 Hz, 1H), 7.23 (d, J=7.5 Hz, 1H), 2.41 (s, 3H).

Process 2; Production of 3-(3-bromo-4-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

To a solution of 19.1 g of 3-bromo-4-methylbenzaldoxime in 100 mL of 1,2-dimethoxyethane, 13.4 g of N-chlorosuccinimide was added and the resultant mixture was stirred at 70° C. for 2 hours. Next, the reaction mixture was left to be cooled down to room temperature and thereto, 16.1 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene, 22.2 g of potassium hydrogen carbonate and 15 mL of water were added, followed by continuing the stirring of the resultant reaction mixture at room temperature further for 20 hours. After the completion of the reaction, the reaction mixture was diluted with 100 mL of ethyl acetate and was washed with water (70 mL×1). Further, the reaction mixture was dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order and the solvent was distilled off under reduced pressure. The resultant residual solid was washed with diisopropyl ether to obtain 20.0 g of the objective substance as a white crystal.

Melting point: 119.0 to 121.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.80 (d, J=1.5 Hz, 1H), 7.5-7.6 (m, 3H), 7.43 (t, J=1.5 Hz, 1H), 7.28 (d, J=8.1 Hz, 1H), 4.05 (d, J=17.4 Hz, 11-1), 3.66 (d, J=17.4 Hz, 1H), 2.43 (s, 3H).

Process 3; Production of 3-(3-bromo-4-(bromomethyl)phenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

To a solution of 20.0 g of 3-(3-bromo-4-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 170 mL of 1,2-dichloroethane, 9.4 g of N-bromosuccinimide and 0.6 g of α,α′-azobisisobutylonitrile were added and the resultant mixture was stirred at 80° C. for 3 hours. After the completion of the reaction, the reaction mixture was left to be cooled down to room temperature and was washed with water (50 mL×2). Subsequently, the reaction mixture was dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order and the solvent was distilled off under reduced pressure to obtain 25.1 g of a crude objective substance as a brown oily substance. This substance was used in the next process without being further purified.

Process 4; Production of N-(2-bromo-4-(5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl) phenylmethyl) phthalimide

To a solution of 12.0 g of 3-(3-bromo-4-(bromomethyl)phenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 80 mL of N,N-dimethylformamide, 4.18 g of potassium phthalimide was added and the resultant mixture was stirred at room temperature for 3 hours. After the completion of the reaction, the reaction mixture was diluted with 120 mL of ethyl acetate and was washed with water (80 mL×3). Subsequently, the reaction mixture was dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:3) to obtain 7.2 g of the objective substance as a light yellow resinoid.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.7-8.1 (m, 4H), 7.35-7.7 (m, 4H), 7.15-7.35 (m, 2H), 4.98 (s, 2H), 4.03 (d, J=17.4 Hz, 1H), 3.65 (d, J=17.4 Hz, 1H).

Process 5; Production of 3-(4-aminomethyl-3-bromophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

To a suspension of 5.94 g of N-(2-bromo-4-(5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)phenylmethyl) phthalimide in 150 mL of ethanol, 3.0 mL of a 80% hydrazine monohydrate aqueous solution was added and the resultant mixture was stirred while heating the reaction mixture to reflux for 2 hours. After the completion of the reaction, the reaction mixture was left to be cooled down to room temperature and thereto, 100 mL of chloroform was added to filter off an insoluble substance, followed by distilling off the solvent under reduced pressure. To the resultant residue, 50 mL of chloroform was added to dissolve the residue and to filter off the resultant insoluble substance. The filtrate was washed with water (50 mL×1) and then was dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure to obtain 3.87 g of the objective substance as a yellow resinoid.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.84 (d, J=1.5 Hz, 11-1), 7.62 (dd, J=8.1, 1.5 Hz, 1H), 7.45-7.55 (m, 3H), 7.43 (t, J=1.5 Hz, 1H), 4.06 (d, J=17.4 Hz, 1H), 3.99 (s, 2H), 3.67 (d, J=17.4 Hz, 1H).

Process 6; Production of N-(2-bromo-4-(5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl) phenylmethyl cyclopropanecarboxamide

Into a solution of 3.87 g of 3-(4-aminomethyl-3-bromophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole and 1.25 g of triethylamine in 60 mL of dichloromethane, 0.30 g of cyclopropanecarbonyl chloride was dropped while ice-cooling and stirring the solution. After the completion of the dropping, the resultant mixture was continuously stirred at room temperature further for 10 minutes. After the completion of the reaction, the solvent was distilled off under reduced pressure and the resultant residue was dissolved in 60 mL of ethyl acetate. The resultant solution was washed with 30 mL of a 2N hydrochloric acid aqueous solution, 30 mL of water and 30 mL of a saturated sodium hydrogen carbonate aqueous solution, and then was dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order, followed by distilling off the solvent under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:4) to obtain 3.40 g of the objective substance as a white crystal.

Melting point: 158.0 to 162.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.83 (s, 1H), 7.4-7.6 (m, 5H), 6.33 (t, J=6.0 Hz, 1H), 4.51 (d, J=6.0 Hz, 2H), 4.05 (d, J=17.4 Hz, 1H), 3.67 (d, J=17.4 Hz, 1H), 1.35-1.5 (m, 1H), 0.85-1.1 (m, 4H).

Process 7; Production of tert-butyl N-(2-bromo-4-(5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl) phenylmethyl)-N-(cyclopropylcarbonyl) carbamate

To a solution of 0.54 g of N-(2-bromo-4-(5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl) phenylmethyl)cyclopropanecarboxamide, 0.10 g of trimethylamine and 0.01 g of 4-(N,N-dimethylamino) pyridine in 20 mL of dichloromethane, 0.44 g of di-tert-butyl dicarbonate was added and the resultant mixture was stirred at room temperature for 17 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure and to the resultant residue, 20 mL of diethyl ether and 5 mL of a 1N sodium hydroxide aqueous solution were added, followed by stirring the reaction mixture at room temperature for 5 minutes. Subsequently, the organic phase was separated off. The aqueous phase was extracted with diethyl ether (10 mL×2) and combined with the organic phase. The combined organic phase was washed with 10 mL of a 2N hydrochloric acid aqueous solution and then was dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order, followed by distilling off the solvent under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:4) to obtain 0.50 g of the objective substance as a colorless resinoid.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.82 (s, 1H), 7.56 (d, J=8.1 Hz, 1H), 7.49 (s, 2H), 7.42 (s, 1H), 7.05 (d, J=8.1 Hz, 1H), 4.95 (s, 2H), 4.04 (d, J=17.1 Hz, 1H), 3.65 (d, J=17.1 Hz, 1H), 2.85-2.95 (m, 1H), 1.44 (s, 9H), 1.1-1.2 (m, 2H), 0.95-1.05 (m, 2H).

Process 8: Production of tert-butyl N-(2-bromo-4-((2Z)-3-(3,5-dichlorophenyl)-1-hydroxyimino-4,4,4-trifluoro-2-butenyl)phenylmethyl)-N-(cyclopropylcarbonyl) carbamate.

Into a solution of 0.47 g of tert-butyl N-(2-bromo-4-(5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl) phenylmethyl)-N-(cyclopropylcarbonyl) carbamate in 15 mL of tetrahydrofuran, 0.74 mL of a 1.0 M lithium hexamethyldisilazane tetrahydrofuran solution was dropped at room temperature with stirring. After the completion of the dropping, the resultant mixture was continuously stirred at the same temperature further for 30 minutes. After the completion of the reaction, the reaction mixture was charged into 10 mL of ice water and thereto, a 2N hydrochloric acid aqueous solution was added, followed by extracting the resultant reaction mixture with ethyl acetate (20 mL×2) under an acidic condition. The organic phase was washed with water and then dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order, followed by distilling off the solvent from the organic phase under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (2:3) to obtain 0.41 g of the objective substance as a colorless resinoid.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.01 (bs, 1H), 7.82 (s, 1H), 7.4-7.45 (m, 4H), 7.04 (d, J=8.1 Hz, 1H), 6.73 (s, 1H), 4.97 (s, 2H), 2.85-3.0 (m, 1H), 1.37 (s, 9H), 1.15-1.2 (m, 2H), 0.95-1.05 (m, 2H).

Synthetic Example 10

Tert-butyl N-(2-bromo-4-(4-bromo-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl) phenylmethyl)-N-(cyclopropylcarbonyl) carbamate (compound of the present invention No. 2-006 in the following Table 8).

To a solution of 0.36 g of tert-butyl N-(2-bromo-4-((2Z)-3-(3,5-dichlorophenyl)-1-hydroxyimino-4,4,4-trifluoro-2-butenyl)phenylmethyl)-N-(cyclopropylcarbonyl) carbamate synthesized in Synthetic Example 9 in 10 mL of benzene, 0.11 g of N-bromosuccinimide was added and the resultant mixture was stirred at room temperature for 16 hours. After the completion of the reaction, an insoluble substance was filtered off and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (2:3) to obtain 0.23 g of the objective substance as a colorless resinoid.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.00 (s, 1H), 7.69 (d, J=8.4 Hz, 1H), 7.4-7.55 (m, 3H), 7.10 (d, J=8.4 Hz, 1H), 5.79 (s, 1H), 4.98 (s, 2H), 2.85-2.95 (m, 1H), 1.41 (s, 9H), 1.1-1.2 (m, 2H), 0.95-1.05 (m, 2H).

Synthetic Example 11

N-(2-bromo-4-(4-bromo-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl) phenylmethyl)cyclopropylcarboxamide (compound of the present invention No. 2-002 in the following Table 8).

To 0.23 g of tert-butyl N-(2-bromo-4-(4-bromo-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl) phenylmethyl)-N-(cyclopropylcarbonyl) carbamate synthesized in Synthetic Example 10, 10 mL of trifluoroacetic acid was added and the resultant mixture was stirred at room temperature for 1 hour. After the completion of the reaction, trifluoroacetic acid was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:1) to obtain 0.15 g of the objective substance as a colorless resinoid.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.03 (s, 1H), 7.70 (d, J=8.4 Hz, 1H), 7.4-7.55 (m, 4H), 6.14 (t, J=6.3 Hz, 1H), 5.80 (s, 1H), 4.56 (d, J=6.3 Hz, 2H), 1.35-1.45 (m, 1H), 0.95-1.05 (m, 2H), 0.75-0.85 (m, 2H).

Synthetic Example 12

N-(2-bromo-4-(5-(3,5-dichlorophenyl)-4-methyl-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl) phenylmethyl)-N-(methyl)cyclopropanecarboxamide (compound of the present invention No. 2-005 in the following Table 8).

In a nitrogen atmosphere, into a solution of 0.54 g of N-(2-bromo-4-(5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl) phenylmethyl)cyclopropanecarboxamide synthesized in Process 6 of Synthetic Example 9 in 5 mL of tetrahydrofuran, 2.0 mL of a 1.0 M lithium hexamethyldisilazane tetrahydrofuran solution was dropped at −78° C. with stirring. After the completion of the dropping, the resultant mixture was continuously stirred at the same temperature further for 30 minutes. Next, to the reaction mixture, 1.42 g of methyl iodide was added and the reaction mixture was heated to room temperature while continuously stirring the reaction mixture further for 15 hours. After the completion of the reaction, the reaction mixture was charged into 5 mL of ice water and thereto, a 2N hydrochloric acid aqueous solution was added, followed by extracting the resultant reaction mixture with ethyl acetate (20 mL×2) under an acidic condition. The organic phase was washed with water and then dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off from the organic phase under reduced pressure, followed by purifying the resultant residue by high performance liquid chromatography eluting with acetonitrile-water (4:1) to obtain 0.19 g of the objective substance as a colorless resinoid.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.98, 7.90, 7.88 and 7.79 (s, 1H), 7.4-7.7 (m, 4H), 7.15-7.3 (m, 1H), 4.65-4.8 (m, 21-1), 3.95-4.1 and 4.1-4.2 (m, 1H), 3.03, 3.05, 3.17 and 3.20 (s, 3H), 1.4-1.55 and 1.8-1.9 (m, 1H), 1.0-1.1 (m, 2H), 0.9-1.05 (m, 3H), 0.65-0.8 and 0.8-0.9 (m, 2H).

Synthetic Example 13

3-(3,5-dichlorophenyl)-4,4,4-trifluoro-1-(4-(methylthio) phenyl)-2-butenone-1-oxime (compound of the present invention No. 9-004 in the following Table 15).

In a nitrogen atmosphere, into a solution of 0.41 g of 5-(3,5-dichlorophenyl)-3-(4-(methylthio) phenyl)-5-trifluoromethyl-4,5-dihydroisoxazole (compound No. 1-002 in Patent Document 5) in 10 mL of tetrahydrofuran, 1.1 mL of a 1.0 M lithium hexamethyldisilazane tetrahydrofuran solution was dropped at room temperature with stirring. After stirring the resultant mixture at room temperature for 10 minutes, the reaction mixture was charged into 5 mL of ice water and thereto, a 2N hydrochloric acid aqueous solution was added, followed by extracting the resultant reaction mixture with diethyl ether (10 mL×2) under an acidic condition. The organic phase was washed with water and then dehydrated and dried over a saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off from the organic phase under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:9) to obtain 0.35 g of the objective substance as a white crystal.

Melting point: 129.0 to 131.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.75 (s, 1H), 7.51 (d, J=8.1 Hz, 2H), 7.43 (s, 3H), 7.2-7.3 (m, 2H), 6.74 (s, 1H), 2.51 (s, 3H).

Synthetic Example 14

4-bromo-5-(3,5-dichlorophenyl)-3-(4-(methylthio) phenyl)-5-trifluoromethyl-4,5-dihydroisoxazole (compound of the present invention No. 4-002 in the following Table 10).

To a solution of 0.18 g of 3-(3,5-dichlorophenyl)-4,4,4-trifluoro-1-(4-(methylthio) phenyl)-2-butenone-1-oxime synthesized in Synthetic Example 13 in 4 mL of benzene, 0.09 g of N-bromosuccinimide was added and the resultant mixture was stirred at room temperature for 19 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:4) to obtain 0.07 g of the objective substance as a white crystal.

Melting point 109.0 to 112.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.65-7.75 (m, 2H), 7.50 (bs, 1H), 7.4-7.45 (m, 2H), 7.25-7.3 (m, 2H), 5.83 (s, 1H), 2.53 (s, 3H).

The compound of the present invention can be produced according to the above production methods and Examples. Examples of the compound of the present invention produced in substantially the same manner as those in Synthetic Example 1 to Synthetic Example 14 are shown in Table 7 to Table 17, which should not be construed as limiting the scope of the present invention.

Here, in Tables, a structure represented by G²-7 represents the following structure:

in Tables, aromatic heterocyclic rings represented by D10-2a to D34-1c individually represent the following structures:

in Tables, an aliphatic heterocyclic ring represented by E4-1a represents the following structure:

in Tables, “Et” represents an ethyl group; “c-Pr” and “Pr-c” individually represent a cyclopropyl group; “t-Bu” and “Bu-t” represent a tertiary butyl group; and a description “Ph” represents a phenyl group,

in Tables, T-4 and T-5 individually represent the structures:

In addition, in Tables, the numbers representing substituted positions of substituents (X)_(m) and (Y)_(n) correspond to the positions of numbers attached to each of the following structural formulae, and an expression “-” represents “non-substituted”. The number representing a substituted position of a substituent (Z^(a))_(p) corresponds to a position of a number attached to the above structural formula, and an expression “-” represents “non-substituted”.

Furthermore, “*1” in Tables means “resinous”.

TABLE 7

No. (X)_(m) R^(3a) (Y)_(n) R² R¹ m.p. (° C.) 1-001 3,5-(CF₃)₂ Br — H H 190.0-193.0 1-002 3,5-Cl₂ Cl 2-CH₃ H CH₂CF₃ 127.0-128.0 1-003 3,5-Cl₂ Br 2-CH₃ H CH₂CF₃ *1 1-004 3,5-Cl₂ CH₃ 2-CH₃ H CH₂CF₃ *1 1-005 3,5-Cl₂ SCH₃ 2-CH₃ H CH₂CF₃ *1 1-006 3,5-(CF₃)₂ Br — H E4-1a *1 1-007 3,5-(CF₃)₂ Br — H CH₂C(O)NHCH₂CF₃ *1 1-008 3,5-Cl₂ Br 2-NO₂ H CH₂C(O)NHCH₂CF₃ *1 1-009 3,5-(CF₃)₂ Br — H CH₂(D10-2a) 155.0-159.0 1-010 3,5-(CF₃)₂ Br — H CH₂(D32-1a) *1 1-011 3,5-(CF₃)₂ Br — H CH═NOCH₃ 118.0-122.0 1-012 3,5-(CF₃)₂ Br — H CH═NOEt *1 1-013 3,4-Cl₂-5-CF₃ Br — H CH═NOEt *1 1-014 3,5-(CF₃)₂ Br — H C(O)OEt 168.0-170.0

TABLE 8

m.p. No. (X)_(m) R^(3a) (Y)_(n) R^(4a) R^(2a) R¹⁴ (° C.) 2-001 3,5-Cl₂ Cl 2-Br H H c-Pr *1 2-002 3,5-Cl₂ Br 2-Br H H c-Pr *1 2-003 3,4,5-Cl₃ Br 2-Br H H c-Pr *1 2-004 3,4,5-Cl₃ Br — CH₃ H c-Pr *1 2-005 3,5-Cl₂ CH₃ 2-Br H CH₃ c-Pr *1 2-006 3,5-Cl₂ Br 2-Br H C(O)OBu-t c-Pr *1

TABLE 9

No. (X)_(m) R^(3a) (Y)_(n) G² (Z^(a))_(p) m.p. (° C.) 3-001 3,5-(CF₃)₂ Br 2-CN G²-7 — *1

TABLE 10

No. (X)_(m) R^(3a) (Y)_(n) Q m.p. (° C.) 4-001 3,5-Cl₂ Br — NO₂ 137.0-139.0 4-002 3,5-Cl₂ Br — SCH₃ 109.0-112.0 4-003 3,5-(CF₃)₂ Br — C(O)OH 202.0-203.0 4-004 3,5-(CF₃)₂ Br — C(O)OCH₃ 123.0-125.0 4-005 3,5-Cl₂ Br 2-CH₃ C(O)OCH₃ 183.0-185.5

TABLE 11

No. (X)_(m) (Y)_(n) R² R¹ m.p. (° C.) 5-001 3,5-Cl₂ 2-CH₃ H CH₂CF₃ 133.0-135.0 5-002 3,5-Cl₂ 2-CH₃ H E4-1a 107.0-111.0 5-003 3,5-Cl₂ 2-CH₃ H CH₂C(O)NHCH₂CF₃ 185.0-189.0 5-004 3,5-Cl₂ 2-CH₃ H CH═NOCH₃(Z) *1 5-005 3,5-(CF₃)₂ 2-CH₃ H CH═NOCH₃(Z) *1 5-006 3,5-Cl₂ 2-CH₃ H Ph *1 5-007 3,5-Cl₂ 2-CH₃ H Ph-4-F 108.0-109.0 5-008 3,5-Cl₂ 2-CH₃ H Ph-4-CN *1 5-009 3,5-Cl₂ 2-CH₃ H (D32-1d)Cl 214.0-216.0 5-010 3,5-Cl₂ 2-CH₃ H (D34-1c)Cl 197.0-200.0

TABLE 12

No. (X)_(m) (Y)_(n) R² R¹ m.p. (° C.) 6-001 3,5-Cl₂ 2-CH₃ H CH₂CF₃ *1 6-002 3,5-Cl₂ 2-CH₃ CH₃ CH═C═CH₂ 172.0-177.0

TABLE 13

No. (X)_(m) (Y)_(n) R^(4a) R^(2a) R¹⁴ m.p. (° C.) 7-001 3,5-Cl₂ 2-Br H H c-Pr *1 7-002 3,4,5-Cl₃ 2-Br H H c-Pr *1 7-003 3,4,5-Cl₃ — CH₃ H c-Pr *1 7-004 3,5-Cl₂ 2-Br H C(O)OBu-t c-Pr *1

TABLE 14

No. (X)_(m) (Y)_(n) G² (Z^(a))_(p) m.p. (° C.) 8-001 3,5-Cl₂ — G²-7 — *1 8-002 3,5-(CF₃)₂ 2-CN G²-7 — 184.0-186.0

TABLE 15

No. (X)_(m) (Y)_(n) Q m.p. (° C.) 9-001 3,4,5-Cl₃ 2-Cl T-4 190.0-193.0 9-002 3,5-Cl₂ 2-Cl T-5 *1 9-003 3,5-Cl₂ — NO₂ 143.0-145.0 9-004 3,5-Cl₂ — SCH₃ 129.0-131.0 9-005 3,5-Cl₂ — S(O)CH₃ 178.0-183.0 9-006 3,5-Cl₂ — SO₂CH₃ 189.0-191.0 9-007 3,5-Cl₂ — C(O)OCH₃ 167.0-169.0 9-008 3,5-(CF₃)₂ — C(O)OCH₃ 115.0-117.0 9-009 3,5-Cl₂ 2-CH₃ C(O)OCH₃ *1

TABLE 16

No. (X)_(m) (Y)_(n) Q m.p. (° C.) 10-001 3,5-Cl₂ — Br 150.0-152.5 10-002 3,5-Cl₂ 2-CH₃ Br 138.0-140.0

TABLE 17

No. (X)_(m) R^(3a) (Y)_(n) m.p. (° C.) 11-001 3,5-Cl₂ H 2-Cl *1

¹H NMR data of the compound among the compounds of the present invention of which melting points or refractive indexes are not described is shown in Table 18.

TABLE 18 No. ¹H NMR(CDCl₃, Me₄Si, 300 MHz) 1-006 δ8.0-8.15 (m, 3H), 7.89 (s, 4H), 6.58 (d, J = 7.5 Hz, 1H), 6.00 (s, 1H), 5.85-6.0 (m, 1H), 3.95-4.1 (m, 1H), 3.8-3.9 (m, 1H), 2.25-2.4 (m, 1H), 1.85-2.1 (m, 3H). 1-007 δ8.0-8.15 (m, 3H), 7.93 (s, 4H), 5.98 (s, 1H), 4.2-4.25 (m, 2H), 3.9-4.05 (m, 2H). 1-008 δ8.50 (s, 1H), 8.15-8.2 (m, 1H), 7.68 (d, J = 7.8 Hz, 1H), 7.50 (s, 3H), 6.8-7.0 (m, 2H), 5.91 (s, 1H), 4.24 (d, J = 5.4 Hz, 2H), 3.9-4.1 (m, 2H). 1-010 δ8.57 (d, J = 4.5 Hz, 1H), 7.9-8.2 (m, 7H), 7.45-7.8 (m, 2H), 7.33 (d, J = 6.9 Hz, 1H), 5.98 (s, 1H), 4.78 (d, J = 4.8 Hz, 2H). 1-012 δ8.89 and 8.63 (d, J = 9.9 Hz, 1H), 7.85-8.2 (m, 6H), 7.82 (d, J = 9.9 Hz, 1H), 5.97 and 5.30 (s, 1H), 4.19 and 4.05 (q, J = 7.2 Hz, 2H), 1.32 and 1.28 (t, J = 7.2 Hz, 3H). 1-013 δ8.90 and 8.64 (d, J = 9.9 Hz, 1H), 7.8-8.0 (m, 7H), 5.93 (s, 1H), 4.19 (q, J = 7.2 Hz, 2H), 1.33 (t, J = 7.2 Hz, 3H). 2-001 δ8.20 and 7.94 (s, 1H), 7.4-7.75 (m, 5H), 6.2-6.35 (m, 1H), 5.82 and 5.64 (s, 1H), 4.54 and 4.51 (d, J = 6.6 Hz, 2H), 1.3-1.5 (m, 1H), 0.9-1.1 (m, 2H), 0.7-0.85 (m, 2H). 2-003 δ7.9-8.1 (m, 1H), 7.25-7.8 (m, 4H), 6.20 (t, J = 6.0 Hz, 1H), 5.81 (s, 1H), 4.56 (d, J = 6.0 Hz, 2H), 1.35-1.5 (m, 1H), 0.9-1.1 (m, 2H), 0.75-0.9 (m, 2H). 2-004 δ7.78 (d, J = 8.4 Hz, 2H), 7.55-7.75 (m, 2H), 7.43 (d, J = 8.4 Hz, 2H), 5.99 (d, J = 7.2 Hz, 1H), 5.85 (s, 1H), 5.1-5.25 (m, 1H), 1.51 (d, J = 7.2 Hz, 3H), 1.3-1.45 (m, 1H), 0.9-1.05 (m, 2H), 0.65-0.8 (m, 2H). 3-001 δ8.93 (s, 1H), 8.2-8.3 (m, 3H), 7.95-8.1 (m, 4H), 5.99 (s, 1H). 5-004 δ9.49 (d, J = 2.4 Hz, 1H), 8.64 (d, J = 9.9 Hz, 1H), 7.75-7.9 (m, 1H), 7.4-7.55 (m, 6H), 6.79 (s, 1H), 3.91 (s, 3H), 2.53 (s, 3H). 5-005 δ9.07 (s, 1H), 8.61 (d, J = 9.6 Hz, 1H), 7.98 (s, 3H), 7.75-7.9 (m, 1H), 7.4-7.6 (m, 3H), 6.88 (s, 1H), 3.92 (s, 3H), 2.55 (s, 3H). 5-006 δ8.97 (s, 1H), 7.55-7.8 (m, 3H), 7.3-7.5 (m, 8H), 7.17 (t, J = 10.0 Hz, 1H), 6.76 (s, 1H), 2.51 (s, 3H), 1.81 (s, 1H). 5-008 δ8.77 (s, 1H), 8.06 (s, 1H), 7.3-7.85 (m, 10H), 6.79 (s, 1H), 2.51 (s, 3H). 7-001 δ8.34 (s, 1H), 7.81 (s, 1H), 7.35-7.55 (m, 5H), 6.71 (s, 1H), 6.15 (t, J = 6.0 Hz, 1H), 4.56 (d, J = 6.0 Hz, 2H), 1.35-1.5 (m, 1H), 1.0-1.1 (m, 2H), 0.75-0.85 (m, 2H). 7-002 δ7.75 (s, 1H), 7.55 (s, 2H), 7.3-7.45 (m, 2H), 6.74 (s, 1H), 6.64 (t, J = 6.0 Hz, 1H), 4.54 (d, J = 6.0 Hz, 2H), 1.4-1.55 (m, 1H), 1.0-1.1 (m, 2H), 0.75-0.85 (m, 2H). 7-003 δ7.55 (s, 2H), 7.52 (d, J = 8.4 Hz, 2H), 7.34 (d, J = 8.4 Hz, 2H), 6.74 (s, 1H), 6.11 (d, J = 8.1 Hz, 1H), 5.21 (qui, J = 7.2 Hz, 1H), 1.50 (d, J = 7.2 Hz, 3H), 1.3-1.45 (m, 1H), 0.95-1.1 (m, 2H), 0.7-0.85 (m, 2H). 8-001 δ8.62 (s, 1H), 8.14 (s, 1H), 7.75-7.8 (m, 5H), 7.45-7.5 (m, 3H), 6.81 (s, 1H). 9-002 δ10.0 (bs, 1H), 7.2-7.7 (m, 16H), 6.66 (s, 1H), 4.71 (s, 2H). 11-001  δ7.3-7.75 (m, 15H), 7.15-7.25 (m, 1H), 4.65 (s, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4 Hz, 1H).

Test Examples

Next, the usefulness of the compound of the present invention as a pest control agent is more specifically described in the following Test Examples which should not be construed as limiting the scope of the present invention.

Test Example 1 Mortality Test for Plutella xylostella

A 10% emulsifiable concentrate of the compound of the present invention (depending on the type of the compound, a 10% wettable powder was subjected to the test) was diluted with water containing a spreader to prepare a drug solution in a concentration of 10 ppm. In this drug solution, a leaf of cabbage was immersed for about 10 seconds and was air-dried and then put into a petri dish. In the petri dish, five 2 instar larvae of Plutella xylostella per petri dish were released and the petri dish was capped and stored in a thermostatic room of 25° C. The number of killed larvae after 6 days was counted and the mortality was calculated from the following calculation formula:

Mortality(%)=(number of killed larvae/number of released larvae)×100.

Here, the test was carried out with two replications.

As the results of the test, among the compounds subjected to the test, the following compounds exhibited the mortality of 80% or more.

The compounds of the present invention: Nos. 1-002, 1-003*, 1-004*, 1-005*, 1-006*, 1-007*, 1-008*, 1-009*, 1-010*, 1-011*, 1-012*, 1-014*, 2-001 to 2-004, 2-005**, 4-001, 4-002*, 4-004*, 5-001*, 5-002 to 5-005, 5-006*, 5-007″, 5-008″, 5-009, 5-010, 6-001**, 7-001*, 7-002, 7-003, 8-001, 8-002*, 9-003*, 9-004**, 9-005**, 9-006**, and 11-001**.

Here, the above mark “*” indicates that the mortality test was performed using a drug solution of 100 ppm concentration and the mark “**” indicates that the mortality test was performed using a drug solution of 500 ppm concentration.

Test Example 2 Mortality Test for Spodoptera litura

A 10% emulsifiable concentrate of the compound of the present invention (depending on the type of the compound, a 10% wettable powder was subjected to the test) was diluted with water containing a spreader to prepare a drug solution in a concentration of 10 ppm. In this drug solution, a leaf of cabbage was immersed for about 10 seconds and was air-dried and then put into a petri dish. In the petri dish, five 2 instar larvae of Spodoptera litura per petri dish were released and the petri dish was capped and stored in a thermostatic room of 25° C. The number of killed larvae after 6 days was counted and the mortality was calculated from the same calculation formula as that in Test Example 1. Here, the test was carried out with two replications.

As the results of the test, among the compounds subjected to the test, the following compounds exhibited the mortality of 80% or more.

The compounds of the present invention: Nos. 1-002, 1-003*, 1-004*, 1-005*, 1-006*, 1-007*, 1-008*, 1-009*, 1-010*, 1-011*, 1-012*, 2-001 to 2-004, 2-005″, 3-001*, 4-002*, 5-001*, 5-004, 5-005, 5-006*, 5-008″, 5-010, 7-001*, 7-002, 7-003, 8-002*, 9-003*, 9-004″, 9-005″, 9-006″, and 11-001**.

Here, the above mark “*” indicates that the mortality test was performed using a drug solution of 100 ppm concentration and the mark “**” indicates that the mortality test was performed using a drug solution of 500 ppm concentration.

Test Example 3 Mortality Test for Helicoverpa Armigera

A 10% emulsifiable concentrate of the compound of the present invention (depending on the type of the compound, a 10% wettable powder was subjected to the test) was diluted with water containing a spreader to prepare a drug solution in a concentration of 100 ppm. In this drug solution, a leaf of cabbage was immersed for about 10 seconds and was air-dried and then put into a petri dish. In the petri dish, one 2 instar larva of Helicoverpa armigera per petri dish was released and the petri dish was capped and stored in a thermostatic room of 25° C. The number of killed larvae after 6 days was counted and the mortality was calculated from the same calculation formula as that in Test Example 1. Here, the test was carried out with 12 replications.

As the results of the test, among the compounds subjected to the test, the following compounds exhibited the mortality of 80% or more.

The compounds of the present invention: Nos. 1-001 to 1-012, 1-014, 2-001 to 2-004, 3-001, 4-002, 5-001 to 5-010, 7-001 to 7-004, 8-001, 9-003, and 10-002.

Test Example 4 Mortality Test for Homona magnanima

A 10% emulsifiable concentrate of the compound of the present invention (depending on the type of the compound, a 10% wettable powder was subjected to the test) was diluted with water containing a spreader to prepare a drug solution in a concentration of 100 ppm. In this drug solution, a leaf of cabbage was immersed for about 10 seconds and was air-dried and then put into a petri dish. In the petri dish, five 2 instar larvae of Homona magnanima per petri dish were released and the petri dish was capped and stored in a thermostatic room of 25° C. The number of killed larvae after 6 days was counted and the mortality was calculated from the same calculation formula as that in Test Example 1. Here, the test was carried out with two replications.

As the results of the test, among the compounds subjected to the test, the following compounds exhibited the mortality of 80% or more.

The compounds of the present invention: Nos. 1-004, 2-001, 2-004, and 5-005.

Test Example 5 Mortality Test for Frankliniella occidentalis

In a styrol cup having an inner diameter of 7 cm, a wet filtration paper was laid and on the paper, a leaf of kidney bean cut out so as to have the same diameter as the inner diameter of the cup was laid, followed by inoculating ten 1 instar larvae of Frankliniella occidentalis per leaf to the leaf. A 10% emulsifiable concentrate of the compound of the present invention (depending on the type of the compound, a 10% wettable powder was subjected to the test) was diluted with water containing a spreader to prepare a drug solution in a concentration of 500 ppm. The drug solution was dusted using a rotary dusting tower in an amount of 2.5 mL per styrol cup and the cup was capped and stored in a thermostatic room of 25° C. The number of killed larvae after 2 days was counted and the mortality was calculated from the same calculation formula as that in Test Example 1. Here, the test was carried out with two replications.

As the results of the test, among the compounds subjected to the test, the following compounds exhibited the mortality of 80% or more.

The compounds of the present invention: Nos. 1-003, 1-004, 1-011, 1-012, 2-001 to 2-004, 4-001, 4-002, and 5-005.

Test Example 6 Mortality Test for Thrips palmi

In a styrol cup having an inner diameter of 7 cm, a wet filtration paper was laid and on the paper, a leaf of kidney bean cut out so as to have the same diameter as the inner diameter of the cup was laid, followed by inoculating ten imagines of Thrips palmi per leaf to the leaf. A 10% emulsifiable concentrate of the compound of the present invention (depending on the type of the compound, a 10% wettable powder was subjected to the test) was diluted with water containing a spreader to prepare a drug solution in a concentration of 100 ppm. The drug solution was dusted using a rotary dusting tower in an amount of 2.5 mL per styrol cup and the cup was capped and stored in a thermostatic room of 25° C. The number of killed imagines after 2 days was counted and the mortality was calculated from the same calculation formula as that in Test Example 1. Here, the test was carried out with two replications.

As the results of the test, among the compounds subjected to the test, the following compounds exhibited the mortality of 80% or more.

The compounds of the present invention: Nos. 1-002 to 1-004, 1-006, 1-007, 1-009 to 1-012, 2-001 to 2-004, 3-001, 5-005, 8-002, and 11-001.

Test Example 7 Mortality Test for Eysarcoris lewisi

A 10% emulsifiable concentrate of the compound of the present invention (depending on the type of the compound, a 10% wettable powder was subjected to the test) was diluted with water containing a spreader to prepare a drug solution in a concentration of 500 ppm. In this drug solution, a leaf sheath of rice was immersed for about 10 seconds and was air-dried and then put into a test tube. In the test tube, five 1 instar larvae of Eysarcoris lewisi per test tube were released and the test tube was capped with a sponge and stored in a thermostatic room of 25° C. The number of killed larvae after 2 days was counted and the mortality was calculated from the same calculation formula as that in Test Example 1. Here, the test was carried out with two replications.

As the results of the test, among the compounds subjected to the test, the following compounds exhibited the mortality of 80% or more.

The compounds of the present invention: Nos. 1-003, 1-004, and 10-002.

Test Example 8 Mortality Test for Nilaparvata lugens

A 10% emulsifiable concentrate of the compound of the present invention (depending on the type of the compound, a 10% wettable powder was subjected to the test) was diluted with water containing a spreader to prepare a drug solution in a concentration of 500 ppm. In this drug solution, a leaf sheath of rice was immersed for about 10 seconds and was air-dried and then put into a test tube. In the test tube, five 2 instar larvae of Nilaparvata lugens per test tube were released and the test tube was capped with a sponge and stored in a thermostatic room of 25° C. The number of killed larvae after 6 days was counted and the mortality was calculated from the same calculation formula as that in Test Example 1. Here, the test was carried out with two replications.

As the results of the test, among the compounds subjected to the test, the following compounds exhibited the mortality of 80% or more.

The compounds of the present invention: Nos. 1-003, 1-007, 1-008, 1-011, 1-012, 2-001, 2-002, 4-001, 4-002, 5-004, and 5-010.

Test Example 9 Mortality Test for Bemisia argentifolii

In a styrol cup having an inner diameter of 7 cm, a wet filtration paper was laid and on the paper, a cut-out leaf of tomato on which Bemisia argentifolii laid eggs (10 eggs/leaf) was laid. A 10% emulsifiable concentrate of the compound of the present invention (depending on the type of the compound, a 10% wettable powder was subjected to the test) was diluted with water containing a spreader to prepare a drug solution in a concentration of 500 ppm. The drug solution was dusted using a rotary dusting tower in an amount of 2.5 mL per styrol cup and the cup was capped and stored in a thermostatic room of 25° C. The number of killed larvae after 6 days was counted and the mortality was calculated from the same calculation formula as that in Test Example 1. Here, the test was carried out with two replications.

As the results of the test, among the compounds subjected to the test, the following compounds exhibited the mortality of 80% or more.

The compounds of the present invention: Nos. 1-003, 1-010 to 1-012, 2-001 to 2-003, 5-004, and 5-005.

Test Example 10 Mortality Test for Myzus persicae

In a glass petri dish having an inner diameter of 3 cm, a wet absorbent cotton was laid and on the cotton, a leaf of cabbage cut out so as to have the same diameter as the inner diameter of the petri dish was laid, followed by releasing four apterous imagines of Myzus persicae on the leaf. After one day, a 10% emulsifiable concentrate of the compound of the present invention (depending on the type of the compound, a 10% wettable powder was subjected to the test) was diluted with water containing a spreader to prepare a drug solution in a concentration of 500 ppm. The drug solution was dusted using a rotary dusting tower (2.5 mg/cm²) and the petri dish was capped and stored in a thermostatic room of 25° C. The number of killed imagines after 6 days was counted and the mortality was calculated from the same calculation formula as that in Test Example 1. Here, the test was carried out with two replications.

As the results of the test, among the compounds subjected to the test, the following compounds exhibited the mortality of 80% or more.

The compounds of the present invention: Nos. 1-003, 1-006 to 1-008, 1-010, 1-011, 1-012, 2-001, 2-002, 3-001, 4-001, 4-002, 5-003, 5-004, 7-002, and 7-003.

Test Example 11 Mortality Test for Planococcus kraunhiae

In a styrol cup having an inner diameter of 7 cm, a wet filtration paper was laid and on the paper, a leaf of kidney bean cut out so as to have the same diameter as the inner diameter of the cup was laid, followed by inoculating ten 1 instar larvae of Planococcus kraunhiae per leaf to the leaf. A 10% emulsifiable concentrate of the compound of the present invention (depending on the type of the compound, a 10% wettable powder was subjected to the test) was diluted with water containing a spreader to prepare a drug solution in a concentration of 500 ppm. The drug solution was dusted using a rotary dusting tower in an amount of 2.5 mL per styrol cup and the cup was capped and stored in a thermostatic room of 25° C. The number of killed larvae after 6 days was counted and the mortality was calculated from the same calculation formula as that in Test Example 1. Here, the test was carried out with two replications.

As the results of the test, among the compounds subjected to the test, the following compounds exhibited the mortality of 80% or more.

The compounds of the present invention: No. 1-003 and 1-004.

Test Example 12 Mortality Test for Aulacophora femoralis

A 10% emulsifiable concentrate of the compound of the present invention (depending on the type of the compound, a 10% wettable powder was subjected to the test) was diluted with water containing a spreader to prepare a drug solution in a concentration of 500 ppm. In this drug solution, a leaf of cucumber was immersed for about 10 seconds and was air-dried and then put into a petri dish. In the petri dish, five 2 instar larvae of Aulacophora femoralis per petri dish were released and the petri dish was capped and stored in a thermostatic room of 25° C. The number of killed larvae after 6 days was counted and the mortality was calculated from the same calculation formula as that in Test Example 1. Here, the test was carried out with two replications.

As the results of the test, among the compounds subjected to the test, the following compounds exhibited the mortality of 80% or more.

The compounds of the present invention: Nos. 1-003, 1-004, and 6-001.

Test Example 13 Mortality Test for Liriomyza trifolii

A 10% emulsifiable concentrate of the compound of the present invention (depending on the type of the compound, a 10% wettable powder was subjected to the test) was diluted with water containing a spreader to prepare a drug solution in a concentration of 500 ppm. In this drug solution, a leaf of kidney bean on which Liriomyza trifolii laid eggs (10 eggs/leaf) and which was cut out to a diameter of 7 cm was immersed for about 10 seconds and was air-dried and then laid on a wet filtration paper laid in a styrol cup having an inner diameter of 7 cm. The styrol cup was capped and stored in a thermostatic room of 25° C. The number of killed larvae after 6 days was counted and the mortality was calculated from the same calculation formula as that in Test Example 1. Here, the test was carried out with two replications.

As the results of the test, among the compounds subjected to the test, the following compounds exhibited the mortality of 80% or more.

The compounds of the present invention: Nos. 1-003 and 1-004.

Test Example 14 Mortality Test for Tetranychus urticae

In a styrol cup having an inner diameter of 7 cm, a wet filtration paper was laid and on the paper, a leaf of kidney bean cut out so as to have the same diameter as the inner diameter of the cup was laid, followed by inoculating ten larvae of Tetranychus urticae per leaf to the leaf. A 10% emulsifiable concentrate of the compound of the present invention (depending on the type of the compound, a 10% wettable powder was subjected to the test) was diluted with water containing a spreader to prepare a drug solution in a concentration of 500 ppm. The drug solution was dusted using a rotary dusting tower in an amount of 2.5 mL per styrol cup and the cup was capped and stored in a thermostatic room of 25° C. The number of killed larvae after 6 days was counted and the mortality was calculated from the same calculation formula as that in Test Example 1. Here, the test was carried out with two replications.

As the results of the test, among the compounds subjected to the test, the following compounds exhibited the mortality of 80% or more.

The compounds of the present invention: Nos. 1-003, 1-006 to 1-008, 1-011, 1-012, 2-001, 2-002, 2-003*, 2-004*, 4-002, 5-002 to 5-004, 7-001, and 7-003.

Here, the above mark “*” indicates that the mortality test was performed using a drug solution of 100 ppm concentration.

Test Example 15 Mortality Test for Aculops pelekassi

In a styrol cup having an inner diameter of 7 cm, a wet filtration paper was laid and on the paper, a leaf of mandarin orange cut out so as to have the same diameter as the inner diameter of the cup was laid, followed by inoculating ten larvae of Aculops pelekassi per leaf to the leaf. A 10% emulsifiable concentrate of the compound of the present invention (depending on the type of the compound, a 10% wettable powder was subjected to the test) was diluted with water containing a spreader to prepare a drug solution in a concentration of 100 ppm. The drug solution was dusted using a rotary dusting tower in an amount of 2.5 mL per styrol cup and the cup was capped and stored in a thermostatic room of 25° C. The number of killed larvae after 6 days was counted and the mortality was calculated from the same calculation formula as that in Test Example 1. Here, the test was carried out with two replications.

As the results of the test, among the compounds subjected to the test, the following compound has exhibited the mortality of 80% or more.

The compound of the present invention: No. 7-002.

Test Example 16 Mortality Test for Polyphagotarsonemus latus

In a styrol cup having an inner diameter of 7 cm, a wet filtration paper was laid and on the paper, a leaf of kidney bean cut out so as to have the same diameter as the inner diameter of the cup was laid, followed by inoculating ten imagines of Polyphagotarsonemus latus per leaf to the leaf. A 10% emulsifiable concentrate of the compound of the present invention (depending on the type of the compound, a 10% wettable powder was subjected to the test) was diluted with water containing a spreader to prepare a drug solution in a concentration of 100 ppm. The drug solution was dusted using a rotary dusting tower in an amount of 2.5 mL per styrol cup and the cup was capped and stored in a thermostatic room of 25° C. The number of killed imagines after 2 days was counted and the mortality was calculated from the same calculation formula as that in Test Example 1. Here, the test was carried out with two replications.

As the results of the test, among the compounds subjected to the test, the following compound has exhibited the mortality of 80% or more.

The compound of the present invention: No. 7-002.

INDUSTRIAL APPLICABILITY

The substituted isoxazoline compound or the substituted enone oxime compound according to the present invention is an extremely useful compound exhibiting excellent pest control activity, particularly excellent insecticidal and miticidal activity and having substantially no adverse effect on non-target organisms such as mammals, fish and beneficial insects. 

1. A substituted isoxazoline compound or a substituted enone oxime compound represented by General Formula (1) or General Formula (2):

(where A¹, A², A³ and A⁴ independently represent a carbon atom or a nitrogen atom, G¹ represents a benzene ring, a nitrogen-containing 6-membered aromatic heterocyclic ring, a furan ring, a thiophene ring or a 5-membered aromatic heterocyclic ring containing two or more heteroatoms selected from an oxygen atom, a sulfur atom and a nitrogen atom, G² represents a structure represented by G²-1 to G²-11:

W represents an oxygen atom or a sulfur atom, L represents —C(R^(4a))(R^(4b))—, —C(R^(4a))(R^(4b))CH₂—, —CH₂C(R^(4a))(R^(4b))—, —N(R^(4c))—, —C(R^(4a))(R^(4b))N(R^(4c))— or a single bond, X represents a halogen atom, a cyano, a nitro, an azide, —SCN, —SF₅, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R⁴, a C₃ to C₈ cycloalkyl, a (C₃ to C₈) cycloalkyl optionally substituted with R⁴, E1 to E19, a C₂ to C₆ alkenyl, a (C₂ to C₆) alkenyl optionally substituted with R⁴, a C₅ to C₁₀ cycloalkenyl, a C₅ to C₁₀ halocycloalkenyl, a C₂ to C₆ alkynyl, a (C₂ to C₆) alkynyl optionally substituted with R⁴, —OH, —OR⁵, —OS(O)₂R⁵, —SH, —S(O)_(r)R⁵, —N(R⁷)R⁶, —N═C(R^(7a))R^(6a), —C(O)R⁸, —C(R⁸)═NOH, —C(R⁸)═NOR⁹, M3, M13, M30, —C(O)OR⁹, —C(O)SR⁹, —C(O)NH₂, —C(O)N(R¹⁰)R⁹, —C(S)OR⁹, —C(S)SR⁹, —C(S)NH₂, —C(S)N(R¹⁰)R⁹, M23 to M26, M28, M29, —S(O)₂OR⁹, —S(O)₂NH₂, —S(O)₂N(R¹⁰)R⁹, —Si(R^(11a))(R^(11b))R¹¹, a phenyl, a phenyl substituted with (Z)_(p1) or D1 to D38, where when m represents an integer of 2 or more, Xs are optionally the same as or different from each other, and further, when two Xs are adjacent to each other, the two Xs adjacent to each other optionally form —CH₂CH₂CH₂—, —CH₂CH₂O—, —CH₂OCH₂—, —OCH₂O—, —CH₂CH₂S—, —CH₂SCH₂—, —CH₂CH₂N(R¹²)—, —CH₂N(R¹²)CH₂—, —CH₂CH₂CH₂CH₂—, —CH₂CH₂CH₂O—, —CH₂CH₂OCH₂—, —CH₂OCH₂O—, —OCH₂CH₂O—, —OCH₂CH₂S—, —CH₂CH═CH—, —OCH═CH—, —SCH═CH—, —N(R¹²)CH═CH—, —OCH═N—, —SCH═N—, —N(R¹²)CH═N—, —N(R¹²)N═CH—, —CH═CHCH═CH—, —OCH₂CH═CH—, —N═CHCH═CH—, —N═CHCH═N— or —N═CHN═CH— to form together with carbon atoms to which each of the two Xs is bonded, a 5-membered ring or a 6-membered ring, and in this case, a hydrogen atom bonded to each carbon atom forming the ring is optionally replaced by Z, further when hydrogen atoms are replaced simultaneously by 2 or more Zs, Zs are optionally the same as or different from each other, Y represents a halogen atom, a cyano, a nitro, an azide, —SCN, —SF₅, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R⁴, a C₃ to C₈ cycloalkyl, a (C₃ to C₈) cycloalkyl optionally substituted with R⁴, E1 to E18, a C₂ to C₆ alkenyl, a (C₂ to C₆) alkenyl optionally substituted with R⁴, a C₂ to C₆ alkynyl, a (C₂ to C₆) alkynyl optionally substituted with R⁴, —OH, —OR⁵, —OS(O)₂R⁵, —SH, —S(O)_(r)R⁵, —NH₂, —N(R⁷)R⁶, —N(R⁷)C(O)R^(8a), —N═C(R^(7a))R^(6a), —C(O)NH₂, —C(O)N(R¹⁰)R⁹, —C(S)NH₂, —C(S)N(R¹⁰)R⁹, —Si(R^(11a))(R^(11b))R¹¹, a phenyl, a phenyl substituted with (Z)_(p1) or D1 to D38, where when n represents an integer of 2 or more, Ys are optionally the same as or different from each other, and further, when two Ys are adjacent to each other, the two Ys adjacent to each other optionally form —CH₂CH₂CH₂—, —CH₂CH₂O—, —CH₂OCH₂—, —OCH₂O—, —CH₂CH₂S—, —CH₂SCH₂—, —SCH₂S—, —CH₂CH₂CH₂CH₂—, —CH₂CH₂CH₂O—, —CH₂CH₂OCH₂—, —CH₂OCH₂O—, —OCH₂CH₂O—, —OCH₂CH₂S—, —SCH₂CH₂S—, —OCH═N—, —SCH═N—, —CH═CHCH═CH—, —CH═CHCH═N—, —CH═CHN═CH—, —CH═NCH═CH— or —N═CHCH═CH— to form together with carbon atoms to which each of the two Ys is bonded, a 5-membered ring or a 6-membered ring, and in this case, a hydrogen atom bonded to each carbon atom forming the ring is optionally replaced by Z, and further when hydrogen atoms are replaced simultaneously by 2 or more Zs, Zs are optionally the same as or different from each other, Z^(a) represents a halogen atom, a cyano, a nitro, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R⁴, —OH, —OR⁵, —OS(O)₂R⁵, —SH, —S(O)_(r)R⁵, —NH₂, —N(R⁷)R⁶, —C(O)R⁸, —C(R⁸)═NOH, —C(R⁸)═NOR⁹, M3, M13, M30, —C(O)OR⁹, —C(O)SR⁹, —C(O)N(R²)R¹, —C(S)OR⁹, —C(S)SR⁹, —C(S)N(R²)R¹, M23 to M26, M28, M29, —S(O)₂OR⁹, —S(O)₂NH₂, —S(O)₂N(R¹⁰)R⁹, —Si(R^(11a))(R^(11b))R¹¹, a phenyl or a phenyl substituted with (Z)_(p1), where when p represents an integer of 2 or more, Z^(a)s are optionally the same as or different from each other, and further, when two Z^(a)s are adjacent to each other, the two Z^(a) adjacent to each other optionally form —CH═CH—CH═CH— to form a fused ring, in this case, a hydrogen atom bonded to each carbon atom forming the ring is optionally replaced by a halogen atom, a cyano group, a nitro group, a C₁ to C₄ alkyl group, a C₁ to C₄ haloalkyl group, a C₁ to C₄ alkoxy group or a C₁ to C₄ alkylthio group, R¹ represents a hydrogen atom, a cyano, a C₁ to C₁₂ alkyl, a (C₁ to C₁₂) alkyl optionally substituted with R¹³, a C₃ to C₁₂ cycloalkyl, a (C₃ to C₁₂) cycloalkyl optionally substituted with R¹³, E2 to E6, E9, E12 to E15, E18, a C₂ to C₁₂ alkenyl, a (C₂ to C₁₂) alkenyl optionally substituted with R¹³, a C₅ to C₁₄ cycloalkenyl, a C₅ to C₁₄ halocycloalkenyl, a C₃ to C₁₂ alkynyl, a (C₃ to C₁₂) alkynyl optionally substituted with R¹³, a C₃ to C₁₂ allenyl, —C(O)R¹⁴, —C(R¹⁴)═NOH, —C(R¹⁴)═NOR¹⁵, M3, M13, M30, —C(R¹⁴)═NN(R¹⁷)R¹⁶, —C(O)OR¹⁵, —C(O)SR¹⁵, —C(O)N(R¹⁷)R¹⁶, —C(O)N(R¹⁷)OR¹⁵, —C(O)N(R¹⁷)N(R¹⁷)R¹⁶, —C(S) R¹⁴, —C(S)OR¹⁵, —C(S)SR¹⁵, —C(S)N(R¹⁷)R¹⁶, —C(═NR¹⁶)OR¹⁵, —C(═NOR¹⁵)OR¹⁵, M7, M17, M23, M26, —C(═NR¹⁶)SR¹⁵, M9, M19, M24, M28, —C(═NR¹⁶)N(R¹⁷)R¹⁶, —C(═NCN)N(R¹⁷)R¹⁶, —C(═NOR¹⁵)N(R¹⁷)R¹⁶, —C(═NNO₂)N(R¹⁷)R¹⁶, M11, M21, M25, M29, —OR¹⁵, —SR¹⁵, —S(O)₂R¹⁵, —S(O)₂N(R¹⁷)R¹⁶, —N(R¹⁷)R¹⁶, —N═C(R^(17a))R^(16a), C(O)ON═C(R^(17a))R^(16a), SN(R¹⁹)R¹⁸, a phenyl, a phenyl substituted with (Z)_(p1), D1 to D25 or D27 to D38, R² represents a hydrogen atom, a cyano, a C₁ to C₁₂ alkyl, a (C₁ to C₁₂) alkyl optionally substituted with R^(13a), a C₃ to C₁₂ cycloalkyl, a C₃ to C₁₂ alkenyl, a C₃ to C₁₂ haloalkenyl, a C₅ to C₁₄ cycloalkenyl, a C₅ to C₁₄ halocycloalkenyl, C₃ to C₁₂ alkynyl, a C₃ to C₁₂ haloalkynyl, —C(O)R^(14a), —C(O)OR^(15a), —C(O)SR^(15a), —C(O)N(R¹⁷)R¹⁶, —C(O)C(O)OR^(15a), —C(S)OR^(15a), —C(S)SR^(15a), —C(S)N(R¹⁷)R¹⁶, —OR¹⁵, —SR¹⁵, —N(R¹⁷)R¹⁶, —N═C(R^(17a))R^(16a) ₅ S(O)₂R^(15a), —S(O)₂N(R¹⁷)R¹⁶, —SN(R¹⁹)R¹⁸, a phenyl, a phenyl substituted with (Z)_(p1), D1, D2 or D32 to D35, or R² together with R¹ optionally forms ═C(R^(2b))R^(1b) or a C₂ to C₇ alkylene chain to form together with a nitrogen atom to which R¹ and R² are bonded, a 3- to 8-membered ring, and in this case, the alkylene chain optionally contains one oxygen atom, sulfur atom or nitrogen atom and is optionally substituted with a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₆ haloalkyl group, a C₁ to C₆ alkoxy(C₁ to C₆) alkyl group, a C₁ to C₆ alkoxy group, a —CHO group, a C₁ to C₆ alkylcarbonyl group, a C₁ to C₆ haloalkylcarbonyl group, a C₁ to C₆ alkoxycarbonyl group, a C₁ to C₆ haloalkoxycarbonyl group, a C₁ to C₆ alkylaminocarbonyl group, a C₁ to C₆ haloalkylaminocarbonyl group, a phenyl group, a phenyl substituted with (Z)_(p1), a D32 group, a D33 group, a D34 group, a D35 group, an oxo group or a thioxo group, and further, when the substituent Y is present adjacent to G², R² together with Y optionally forms —CH₂—, —CH₂CH₂—, —CH₂O—, —CH₂S—, —CH₂N(R⁶)—, —CH═CH— or —CH═N— to form together with atoms to which each of R² and Y is bonded, a 5-membered ring or a 6-membered ring, and in this case, a hydrogen atom bonded to each carbon atom forming the ring is optionally replaced by a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₆ haloalkyl group, a C₁ to C₆ alkylidene group, a C₁ to C₆ haloalkylidene group, an oxo group or a thioxo group, R^(1a) represents —C(O)R¹⁴, —C(O)OR¹⁵, —C(O)SR¹⁵, —C(O)N(R¹⁷)R¹⁶, —C(O)N(R¹⁷)OR¹⁵, —C(O)N(R¹⁷)N(R¹⁷)R¹⁶, —C(S)R¹⁴, —C(S)OR¹⁵, —C(S)SR¹⁵, —C(S)N(R¹⁷)R¹⁶, —C(SR¹⁵)═NCN, —C(SR¹⁵)═NNO₂, —S(O)₂R¹⁵ or —S(O)₂N(R¹⁷)R¹⁶, R^(2a) represents a hydrogen atom, a cyano, a C₁ to C₁₂ alkyl, a (C₁ to C₁₂) alkyl optionally substituted with R^(13a), a C₃ to C₁₂ cycloalkyl, a C₃ to C₁₂ alkenyl, a C₃ to C₁₂ haloalkenyl, a C₃ to C₁₂ alkynyl, a C₃ to C₁₂ haloalkynyl, —C(O)R^(14a), —C(O)OR^(15a), —C(O)SR^(15a), —C(O)N(R¹⁷)R¹⁶, —C(O)C(O)OR^(15a), —C(S)OR^(15a), —C(S)SR^(15a), —C(S)N(R¹⁷)R¹⁶, a C₁ to C₁₂ alkoxy, a C₁ to C₁₂ haloalkoxy, —SR¹⁵, —S(O)₂R^(15a), —SN(R¹⁹)R¹⁸, a phenyl, a phenyl substituted with (Z)_(p1), D1, D2 or D32 to D35, or R^(2a) together with R^(1a) optionally forms a C₃ to C₆ alkylene chain to form together with a nitrogen atom to which R^(1a) and R^(2a) are bonded, a 4- to 7-membered ring, and in this case, the alkylene chain optionally contains one oxygen atom, sulfur atom or nitrogen atom and is optionally substituted with a C₁ to C₆ alkyl group, a C₁ to C₆ alkylidene group, a —CHO group, a C₁ to C₆ alkylcarbonyl group, a C₁ to C₆ haloalkylcarbonyl group, a C₁ to C₆ alkoxycarbonyl group, a C₁ to C₆ haloalkoxycarbonyl group, a C₁ to C₆ alkylaminocarbonyl group, a C₁ to C₆ haloalkylaminocarbonyl group, a di(C₁ to C₆ alkyl)aminocarbonyl group, a phenyl group, a D32 group, a D34 group, an oxo group or a thioxo group, Rib R^(1b) represents a hydrogen atom, R¹⁴, —OR¹⁵, —SR¹⁵, —S(O)₂R¹⁵ or —N(R^(17b))R^(16b), R^(2b) represents a C₁ to C₆ alkyl, —OR^(15a), —SR^(15a), —SC(O)R^(14a), —SC(O)OR^(15a) or —N(R^(17c))R^(16c), or R^(2b) together with R^(1b) optionally forms a C₄ to C₅ alkylene chain or a C₄ to C₅ alkenylene chain to form together with a carbon atom to which R^(1b) and R^(2b) are bonded, a 5- or 6-membered ring, and in this case, the alkylene chain or the alkenylene chain optionally contains one to three oxygen atom(s), sulfur atom(s) or nitrogen atom(s) and is optionally substituted with a halogen atom, a cyano group, a nitro group, a C₁ to C₆ alkyl group, a C₁ to C₆ haloalkyl group, a C₁ to C₆ alkoxy group, a C₁ to C₆ haloalkoxy group, a C₁ to C₆ alkylthio group, a C₁ to C₆ haloalkylthio group or a R^(17c) group, R³ represents a halogen atom, a cyano, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R⁴, a C₃ to C₈ cycloalkyl, a (C₃ to C₈) cycloalkyl optionally substituted with R⁴, E1 to E19, a C₃ to C₆ alkenyl, a (C₂ to C₆) alkenyl optionally substituted with R⁴, a C₃ to C₆ alkynyl, a (C₂ to C₆) alkynyl optionally substituted with R⁴, —OR⁵, —S(O)_(r)R⁵, —N(R¹⁰)R⁹, —C(O)R⁸, —C(R⁸)═NOH, —C(R⁸)═NOR⁹, M3, M13, M30, —C(O)OR⁹, —C(O)SR⁹, —C(O)NH₂, —C(O)N(R¹⁰)R⁹, —C(S)OR⁹, —C(S)SR⁹, —C(S)NH₂, —C(S)N(R¹⁰)R⁹, —Si(R^(11a))(R^(11b))R¹¹, —P(O)(OR²⁰)₂, a phenyl, a phenyl substituted with (Z)_(p1) or D1 to D38, R^(3a) represents a halogen atom, a cyano, a nitro, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R⁴, a C₃ to C₈ cycloalkyl, a C₂ to C₆ alkenyl, a C₂ to C₆ alkynyl, —C(O)OR⁹, —C(O)SR⁹, —C(O)NH₂, —C(O)N(R¹⁰)R⁹, —C(S)OR⁹, —C(S)SR⁹, —C(S)NH₂, —C(S)N(R¹⁰)R⁹, a C₁ to C₆ alkylthio, a C₁ to C₆ haloalkylthio or a phenyl, R^(3b) represents a hydrogen atom, a halogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₃ to C₆ alkenyl or a C₃ to C₆ alkynyl, R^(3c) represents a hydrogen atom or R^(3a), D1 to D38 individually represent an aromatic heterocyclic ring represented by the following Structural Formulae:

Z represents a halogen atom, a cyano, a nitro, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₁ to C₄ alkoxy(C₁ to C₄) alkyl, a C₁ to C₄ haloalkoxy(C₁ to C₄) alkyl, a C₁ to C₄ alkylthio(C₁ to C₄) alkyl, a C₁ to C₄ haloalkylthio(C₁ to C₄) alkyl, a C₁ to C₄ alkylsulfinyl(C₁ to C₄) alkyl, a C₁ to C₄ haloalkylsulfinyl(C₁ to C₄) alkyl, a C₁ to C₄ alkylsulfonyl(C₁ to C₄) alkyl, a C₁ to C₄ haloalkylsulfonyl(C₁ to C₄) alkyl, a C₃ to C₆ cycloalkyl, a C₃ to C₆ halocycloalkyl, —OH, a C₁ to C₆ alkoxy, a C₁ to C₆ haloalkoxy, a C₁ to C₆ alkyl sulfonyloxy, a C₁ to C₆ haloalkylsulfonyloxy, a C₁ to C₆ alkylthio, a C₁ to C₆ haloalkylthio, a C₁ to C₆ alkylsulfinyl, a C₁ to C₆ haloalkylsulfinyl, a C₁ to C₆ alkylsulfonyl, a C₁ to C₆ haloalkylsulfonyl, —NH₂, a C₁ to C₆ alkylamino, a di(C₁ to C₆ alkyl)amino, a C₁ to C₆ alkoxycarbonyl, a C₁ to C₆ haloalkoxycarbonyl, —C(O)NH₂, a C₁ to C₆ alkylaminocarbonyl, a C₁ to C₆ haloalkylaminocarbonyl, a di(C₁ to C₆ alkyl)aminocarbonyl, —C(S)NH₂, —S(O)₂NH₂, a C₁ to C₆ alkylaminosulfonyl, a di(C₁ to C₆ alkyl)aminosulfonyl, a phenyl or a phenyl optionally substituted with a halogen atom, where when p and p1 individually represent an integer of 2 or more, Zs are optionally the same as or different from each other, and further, when two Zs are adjacent to each other, the two Zs adjacent to each other optionally form —CH₂CH₂CH₂—, —CH₂CH₂O—, —CH₂OCH₂—, —OCH₂O—, —CH₂CH₂S—, —CH₂SCH₂—, —CH₂CH₂CH₂CH₂—, —CH₂CH₂CH₂O—, —CH₂CH₂OCH₂—, —CH₂OCH₂O—, —OCH₂CH₂O—, —CH₂CH₂CH₂S—, —OCH₂CH₂S— or —CH═CH—CH═CH— to form together with carbon atoms to which each of the two Zs is bonded, a 5-membered ring or a 6-membered ring, and in this case, a hydrogen atom bonded to each carbon atom forming the ring is optionally replaced by a halogen atom, a cyano group, a nitro group, a C₁ to C₄ alkyl group, a C₁ to C₄ haloalkyl group, a C₁ to C₄ alkoxy group or a C₁ to C₄ alkylthio group, E1 to E19 individually represent a saturated heterocyclic ring represented by the following Structural Formulae:

R⁴ represents a halogen atom, a cyano, a C₃ to C₈ cycloalkyl, a C₃ to C₈ halocycloalkyl, E1 to E19, —OH, —OR⁵, —SH, —S(O)_(r)R⁵, —N(R⁷)R⁶, —N(R⁷)C(O)R^(8a), —C(O)OR⁹, —C(O)N(R¹⁰)R⁹, —Si(R^(11a))(R^(11b))R¹¹, a phenyl, a phenyl substituted with (Z)_(p1) or D1 to D38, R^(4a) represents a hydrogen atom, a cyano, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₃ to C₆ cycloalkyl, a C₂ to C₆ alkenyl, a C₂ to C₄ alkynyl, a C₁ to C₆ alkoxycarbonyl, —C(O)NH₂, —C(S)NH₂, a phenyl, a phenyl substituted with (Z)_(p1), D1, D2, D9, D10 or D32, R^(4b) represents a hydrogen atom or a C₁ to C₆ alkyl, or R^(4b) together with R^(4a) optionally forms a C₂ to C₅ alkylene chain to form together with a carbon atom to which R^(4a) and R^(4b) are bonded, a 3- to 6-membered ring, and in this case, the alkylene chain optionally contains one oxygen atom, sulfur atom or nitrogen atom and is optionally substituted with a C₁ to C₆ alkyl group, a —CHO group, a C₁ to C₆ alkylcarbonyl group, a C₁ to C₆ alkoxycarbonyl group, a C₁ to C₆ alkylaminocarbonyl group, a C₁ to C₆ haloalkylaminocarbonyl group or a phenyl group, R^(4c) represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₁ to C₆ alkylcarbonyl, a C₁ to C₆ haloalkylcarbonyl, a C₃ to C₆ cycloalkylcarbonyl, a C₃ to C₆ halocycloalkylcarbonyl, a C₁ to C₆ alkoxycarbonyl or a C₁ to C₆ haloalkoxycarbonyl, R⁵ represents a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R²³, a C₃ to C₈ cycloalkyl, a (C₃ to C₈) cycloalkyl optionally substituted with R²³, E2 to E6, E12 to E15, E18, a C₂ to C₆ alkenyl, a (C₂ to C₆) alkenyl optionally substituted with R²³, a C₅ to C₁₀ cycloalkenyl, a C₅ to C₁₀ halocycloalkenyl, a C₃ to C₆ alkynyl, a (C₃ to C₆) alkynyl optionally substituted with R²³, a C₁ to C₆ alkylcarbonyl, a C₁ to C₆ alkoxycarbonyl, a phenyl, a phenyl substituted with (Z)_(p1), D1, D2, D4 to D6, D8 to D10, D12 to D19, D21, D23, D25, D27 or D30 to D38, R⁶ represents a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R²³, a C₃ to C₈ cycloalkyl, a C₃ to C₈ halocycloalkyl, a C₃ to C₆ alkenyl, a C₃ to C₆ haloalkenyl, a C₃ to C₆ alkynyl, a C₃ to C₆ haloalkynyl, —C(O)R⁸, —C(O)OR⁹, —C(O)SR⁹, —C(O)NH₂, —C(O)N(R¹⁰)R⁹, —C(S)OR⁹, —C(S)SR⁹, —C(S)NH₂, —C(S)N(R¹⁰)R⁹, —C(O)C(O)R⁹, —C(O)C(O)OR⁹, —OH, —S(O)₂R⁹, —S(O)₂N(R¹⁰)R⁹, —P(O)(OR²⁰)₂ or —P(S)(OR²⁰)₂, R⁷ represents a hydrogen atom, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R²³, a C₃ to C₈ cycloalkyl, a C₃ to C₆ alkenyl, a C₃ to C₆ haloalkenyl, a C₃ to C₆ alkynyl, a C₃ to C₆ haloalkynyl, —CHO, a C₁ to C₆ alkylcarbonyl, a C₁ to C₆ haloalkylcarbonyl or a C₁ to C₆ alkoxycarbonyl, or R⁷ together with R⁶ optionally forms a C₂ to C₆ alkylene chain to form together with a nitrogen atom to which R⁶ and R⁷ are bonded, a 3- to 7-membered ring, and in this case, the alkylene chain optionally contains one oxygen atom, sulfur atom or nitrogen atom and is optionally substituted with a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₆ haloalkyl group, an oxo group or a thioxo group, R^(6a) represents a C₁ to C₆ alkyl, a C₁ to C₆ alkoxy, a C₁ to C₆ haloalkoxy, a C₃ to C₆ alkenyloxy, a phenoxy or a phenoxy substituted with (Z)_(p1), R^(7a) represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₃ to C₆ alkenyl, a phenyl or a phenyl substituted with (Z)_(p1), or R^(7a) together with R^(6a) optionally forms a C₄ to C₆ alkylene chain to form together with a carbon atom to which R^(6a) and R^(7a) are bonded, a 5- to 7-membered ring, and in this case, the alkylene chain optionally contains one oxygen atom or sulfur atom, R⁸ represents a hydrogen atom, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R²³, a C₃ to C₈ cycloalkyl, a C₃ to C₈ halocycloalkyl, E4 to E6, E12 to E14, a C₃ to C₆ alkenyl, a C₃ to C₆ haloalkenyl, a C₅ to C₁₀ cycloalkenyl, a C₅ to C₁₀ halocycloalkenyl, a C₃ to C₆ alkynyl or a C₃ to C₆ haloalkynyl, R^(8a) represents a phenyl, a phenyl substituted with (Z)_(p1), or D1 to D38, R⁹ represents a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R²³, a C₃ to C₈ cycloalkyl, a C₃ to C₈ halocycloalkyl, E2 to E6, E12 to E19, a C₃ to C₆ alkenyl, a C₃ to C₆ haloalkenyl, a C₃ to C₆ alkynyl, a C₃ to C₆ haloalkynyl, a phenyl, a phenyl substituted with (Z)_(p1), D1 to D25 or D27 to D38, R¹⁰ represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₃ to C₆ cycloalkyl(C₁ to C₄) alkyl, a C₁ to C₆ alkoxy(C₁ to C₄) alkyl, a C₁ to C₆ alkylthio(C₁ to C₄) alkyl, a cyano(C to C₆) alkyl, a C₃ to C₆ alkenyl or a C₃ to C₆ alkynyl, or R¹⁰ together with R⁹ optionally forms a C₂ to C₆ alkylene chain to form together with a nitrogen atom to which R⁹ and R¹⁰ are bonded, a 3- to 7-membered ring, and in this case, the alkylene chain optionally contains one oxygen atom, sulfur atom or nitrogen atom and is optionally substituted with a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₆ alkoxy group, a —CHO group, a C₁ to C₆ alkylcarbonyl group or a C₁ to C₆ alkoxycarbonyl group, R¹¹ represents a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₁ to C₆ alkoxy, a phenyl or a phenyl substituted with (Z)_(p1), R^(11a) and R^(11b) independently represent a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl or a C₁ to C₆ alkoxy, R¹² represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₁ to C₆ alkoxycarbonyl(C₁ to C₄) alkyl, a C₁ to C₆ haloalkoxycarbonyl(C₁ to C₄) alkyl, a phenyl(C₁ to C₄) alkyl, a phenyl(C₁ to C₄) alkyl substituted with (Z)_(p1), a C₂ to C₆ alkenyl, a C₂ to C₆ haloalkenyl, a C₃ to C₆ alkynyl, a C₃ to C₆ haloalkynyl, a C₁ to C₆ alkoxy, a C₁ to C₆ alkoxylcarbonyl, a C₁ to C₆ haloalkoxycarbonyl, a phenyl or a phenyl substituted with (Z)_(p1), and further, when Z is present adjacent to R¹², R¹² and Z adjacent to each other optionally form —CH₂CH₂CH₂CH₂—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —CH═CH—N═CH— or —CH═CH—CH═N— to form together with atoms to which each of R¹² and Z is bonded, a 6-membered ring, and in this case, a hydrogen atom bonded to each carbon atom forming the ring is optionally replaced by a halogen atom, a C₁ to C₄ alkyl group or a C₁ to C₄ haloalkyl group, R¹³ and R^(13a) independently represent a halogen atom, a cyano, a nitro, a C₃ to C₈ cycloalkyl, a C₃ to C₈ halocycloalkyl, a hydroxy(C₃ to C₈) cycloalkyl, a C₁ to C₄ alkoxy(C₃ to C₈) cycloalkyl, E1 to E19, a C₅ to C₁₀ cycloalkenyl, a C₅ to C₁₀ halocycloalkenyl, —OR²⁴, —N(R²⁵)R²⁴, —SH, —S(O)_(r)R²⁶, —C(O)R²⁷, —C(R²⁷)═NOH, —C(R²⁷)═NOR²⁸, —C(O)OH, —C(O)OR²⁸, —C(O)SR²⁸, —C(O)NH₂, —C(O)N(R²⁹)R²⁸, —C(O)N(R²⁹)OR²⁸, —C(O)N(R²⁹)N(R²⁹)R²⁸, —C(O)C(O)OR²⁸, —C(S)OR²⁸, —C(S)SR²⁸, —C(S)NH₂, —C(S)N(R²⁹)R²⁸, —C(═NR²⁹)OR²⁸, —C(═NR²⁹)SR²⁸, —C(═NR²⁹)N(R²⁹)R²⁸, —C(═NOR²⁸)N(Z²⁹)R²⁸, —S(O)₂OH, —S(O)₂NH₂, —S(O)₂N(R²⁹)R²⁸, —Si(R^(11a))(R^(11b))R¹¹, —P(O)(OR²⁰)₂, —P(S)(OR²⁰)₂, —P(phenyl)₂, —P(O)(phenyl)₂, M1 to M30, a phenyl, a phenyl substituted with (Z)_(p1), a naphthyl or D1 to D38, M1 to M30 individually represent a partially saturated heterocyclic ring represented by the following Structural Formulae:

R¹⁴ and R^(14a) independently represent a hydrogen atom, a C₁ to C₁₂ alkyl, a (C₁ to C₁₂) alkyl optionally substituted with R³⁰, a C₃ to C₁₂ cycloalkyl, a (C₃ to C₁₂) cycloalkyl optionally substituted with R³⁰, E1 to E19, a C₂ to C₁₂ alkenyl, a (C₂ to C₁₂) alkenyl optionally substituted with R³⁰, a C₅ to C₁₂ cycloalkenyl, a C₅ to C₁₂ halocycloalkenyl, a C₂ to C₁₂ alkynyl, a (C₂ to C₁₂) alkynyl optionally substituted with R³⁰, —C(O)R²⁷, —C(R²⁷)═NOH, —C(R²⁷)═NOR²⁸, —C(R²⁷)═NN(R²⁹)R²⁸, —C(O)OR²⁸, —C(O)N(R²⁹)R²⁸, M4, a phenyl, a phenyl substituted with (Z)_(p1), a naphthyl or D1 to D38, R¹⁵ and R^(15a) independently represent a C₁ to C₁₂ alkyl, a (C₁ to C₁₂) alkyl optionally substituted with R³⁰, a C₃ to C₁₂ cycloalkyl, a (C₃ to C₁₂) cycloalkyl optionally substituted with R³⁰, E2 to E6, E12 to E19, a C₂ to C₁₂ alkenyl, a C₂ to C₁₂ haloalkenyl, a C₅ to C₁₀ cycloalkenyl, a C₅ to C₁₀ halocycloalkenyl, a C₃ to C₁₂ alkynyl, a C₂ to C₁₂ haloalkynyl, a phenyl, a phenyl substituted with (Z)_(p1), D1, D2, D4 to D6, D8 to D10, D12 to D19, D21, D23, D25, D27 or D30 to D38, R¹⁶ represents a hydrogen atom, a C₁ to C₁₂ alkyl, a (C₁ to C₁₂) alkyl optionally substituted with R³⁰, a C₃ to C₁₂ cycloalkyl, a (C₃ to C₁₂) cycloalkyl optionally substituted with R³⁰, E2 to E6, E12 to E19, a C₂ to C₁₂ alkenyl, a C₂ to C₁₂ haloalkenyl, a C₅ to C₁₀ cycloalkenyl, a C₅ to C₁₀ halocycloalkenyl, a C₃ to C₁₂ alkynyl, a C₂ to C₁₂ haloalkynyl, —C(O)R²⁷, —C(O)OR²⁸, —C(O)SR²⁸, —C(O)NH₂, —C(O)N(R²⁹)R²⁸, —C(S)R²⁷, —C(S)OR²⁸, —C(S)SR²⁸, —C(S)NH₂, —C(S)N(R²⁹)R²⁸, M7, M9, M17, M19, —S(O)₂R²⁸, —S(O)₂NH₂, —S(O)₂N(R²⁹)R²⁸, —P(O)(OR²⁰)₂, —P(S)(OR²⁰)₂, a phenyl, a phenyl substituted with (Z)_(p1), D1 to D25 or D27 to D38, R¹⁷ represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₃ to C₆ cycloalkyl(C₁ to C₄) alkyl, a C₁ to C₄ alkoxy(C₁ to C₄) alkyl, a C₁ to C₄ haloalkoxy(C₁ to C₄) alkyl, a C₁ to C₄ alkylthio(C₁ to C₄) alkyl, a C₁ to C₄ haloalkylthio(C₁ to C₄) alkyl, a C₁ to C₄ alkylsulfonyl(C₁ to C₄) alkyl, a C₁ to C₄ haloalkylsulfonyl(C₁ to C₄) alkyl, a cyano(C₁ to C₆) alkyl, a C₁ to C₄ alkoxycarbonyl(C₁ to C₄) alkyl, a phenyl(C₁ to C₄) alkyl, a C₂ to C₆ alkenyl, a C₂ to C₆ haloalkenyl, a C₃ to C₆ alkynyl or a C₃ to C₆ haloalkynyl, or R¹⁷ together with R¹⁶ optionally forms a C₂ to C₆ alkylene chain to form together with a nitrogen atom to which R¹⁶ and R¹⁷ are bonded, a 3- to 7-membered ring, and in this case, the alkylene chain optionally contains one oxygen atom, sulfur atom or nitrogen atom and is optionally substituted with a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₄ alkoxy(C₁ to C₄) alkyl group, a C₁ to C₆ alkoxy group, a —CHO group, a C₁ to C₆ alkylcarbonyl group, a C₁ to C₆ alkoxycarbonyl group, an oxo group or a thioxo group, R^(16a) represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₁ to C₄ alkoxy(C₁ to C₄) alkyl, a C₁ to C₄ alkylthio(C₁ to C₄) alkyl, a C₁ to C₄ alkylsulfonyl(C₁ to C₄) alkyl, a C₁ to C₄ alkoxycarbonyl(C₁ to C₄) alkyl, a phenyl(C₁ to C₄) alkyl, a phenyl(C₁ to C₄) alkyl substituted with (Z)_(p1), a C₃ to C₆ cycloalkyl, E1 to E19, a phenyl(C₂ to C₄) alkenyl, a di(C₁ to C₆ alkyl)amino, a phenyl, a phenyl substituted with (Z)_(p1) or D1 to D38, R^(17a) represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ alkoxy, a C₁ to C₆ alkylthio or a di(C₁ to C₆ alkyl)amino, or R^(17a) together with R^(16a) optionally forms a C₃ to C₅ alkylene chain to form together with a carbon atom to which R^(16a) and R^(17a) are bonded, a 4- to 6-membered ring, and in this case, the alkylene chain optionally contains one oxygen atom, sulfur atom or nitrogen atom and is optionally substituted with a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₆ haloalkyl group, a —CHO group, a C₁ to C₆ alkylcarbonyl group or a C₁ to C₆ alkoxycarbonyl group, R^(16b) represents a hydrogen atom, a cyano, a nitro, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl or a C₁ to C₆ alkoxy, R^(17b) represents a hydrogen atom or a C₁ to C₆ alkyl, or R^(17b) together with R^(16b) optionally forms a C₃ to C₅ alkylene chain to form together with a nitrogen atom to which R^(16b) and R^(17b) are bonded, a 4- to 6-membered ring, and in this case, the alkylene chain optionally contains one oxygen atom, sulfur atom or nitrogen atom and is optionally substituted with a C₁ to C₆ alkyl group, a —CHO group, a C₁ to C₆ alkylcarbonyl group or a C₁ to C₆ alkoxycarbonyl group, R^(16c) represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₃ to C₆ alkenyl, a C₃ to C₆ alkynyl, a C₁ to C₆ alkoxy, a C₁ to C₆ haloalkoxy, —NH₂, a C₁ to C₆ alkylamino, a di(C₁ to C₆ alkyl)amino, —NHC(O)R²⁷, —NHC(O)OR²⁸, —NHC(O)SR²⁸, —NHC(O)NH₂, —NHC(O)N(R²⁹)R²⁸, —NHC(S)OR²⁸, —NHC(S)SR²⁸, —NHC(S)NH₂, —NHC(S)N(R²⁹)R²⁸, —NHS(O)₂R²⁸, —NHS(O)₂NH₂ or —NHS(O)₂N(R²⁹)R²⁸, R^(17c) represents a hydrogen atom or a C₁ to C₆ alkyl, or R^(17c) together with R^(16c) optionally forms a C₃ to C₅ alkylene chain to form together with a nitrogen atom to which R^(16c) and R^(17c) are bonded, a 4- to 6-membered ring, and in this case, the alkylene chain optionally contains one oxygen atom, sulfur atom or nitrogen atom and is optionally substituted with a C₁ to C₆ alkyl group, a —CHO group, a C₁ to C₆ alkylcarbonyl group or a C₁ to C₆ alkoxycarbonyl group, R¹⁸ represents a C₁ to C₁₂ alkyl, a C₁ to C₁₂ haloalkyl, a C₁ to C₁₂ alkoxy(C₁ to C₁₂) alkyl, a cyano(C₁ to C₁₂) alkyl, a C₁ to C₁₂ alkoxycarbonyl(C₁ to C₁₂) alkyl, a phenyl(C₁ to C₄) alkyl, a phenyl(C₁ to C₄) alkyl substituted with (Z)_(p1), a C₃ to C₁₂ alkenyl, a C₃ to C₁₂ haloalkenyl, a C₃ to C₁₂ alkynyl, a C₃ to C₁₂ haloalkynyl, a C₁ to C₁₂ alkylcarbonyl, a C₁ to C₁₂ alkoxycarbonyl, —C(O)ON═C(CH₃)SCH₃, —C(O)ON═C(SCH₃)C(O)N(CH₃)₂, a phenyl or a phenyl substituted with (Z)_(p1), R¹⁹ represents a C₁ to C₁₂ alkyl, a C₁ to C₁₂ haloalkyl, a C₁ to C₁₂ alkoxy(C₁ to C₁₂) alkyl, a cyano(C₁ to C₁₂) alkyl, a C₁ to C₁₂ alkoxycarbonyl(C₁ to C₁₂) alkyl, a phenyl(C₁ to C₄)alkyl, a phenyl(C₁ to C₄) alkyl substituted with (Z)_(p1), a C₃ to C₁₂ alkenyl, a C₃ to C₁₂ haloalkenyl, a C₃ to C₁₂ alkynyl, a C₃ to C₁₂ haloalkynyl, a phenyl or a phenyl substituted with (Z)_(p1), or R¹⁹ together with R¹⁸ optionally forms a C₄ to C₇ alkylene chain to form together with a nitrogen atom to which R¹⁸ and R¹⁹ are bonded, a 5- to 8-membered ring, and in this case, the alkylene chain optionally contains one oxygen atom or sulfur atom and is optionally substituted with a C₁ to C₄ alkyl group or a C₁ to C₄ alkoxy group, R²⁰ represents a C₁ to C₆ alkyl or a C₁ to C₆ haloalkyl, R²¹ represents a halogen atom, a cyano, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a hydroxy(C₁ to C₆) alkyl, a C₁ to C₄ alkoxy(C₁ to C₄) alkyl, a C₁ to C₄ alkoxycarbonyl(C₁ to C₄)alkyl, a C₁ to C₆ alkoxy, a C₁ to C₆ alkylthio, a C₁ to C₆ alkylamino, a di(C₁ to C₄ alkyl)amino, a C₁ to C₆ alkoxycarbonyl, a phenyl or a phenyl substituted with (Z)_(p1), where when q represents an integer of 2 or more, R²¹s are optionally the same as or different from each other, and further when two R²¹s are replaced on the same carbon atom, the two R²¹s together with each other optionally form an oxo, a thioxo, an imino, a C₁ to C₆ alkylimino, a C₁ to C₆ alkoxyimino or a C₁ to C₆ alkylidene, R²² represents a hydrogen atom, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R³⁰, a C₃ to C₆ cycloalkyl, a C₃ to C₆ alkenyl, a C₃ to C₆ haloalkenyl, a C₃ to C₆ alkynyl, —OH, a benzyloxy, —C(O)R³¹, —C(O)OR³², —C(O)SR³², —C(O)N(R³⁴)R³³, —C(S)N(R³⁴)R³³, —S(O)₂R³², —P(O)(OR²⁰)₂, —P(S)(OR²⁰)₂, a phenyl, a phenyl substituted with (Z)_(/31) or D3, R²³ represents a halogen atom, a cyano, a C₃ to C₈ cycloalkyl, a C₃ to C₈ halocycloalkyl, E1 to E19, a C₁ to C₆ alkoxy, a C₁ to C₆ haloalkoxy, a C₁ to C₆ alkylthio, a C₁ to C₆ haloalkylthio, a C₁ to C₆ alkylsulfonyl, a C₁ to C₆ haloalkylsulfonyl, a C₁ to C₆ alkylamino, a di(C₁ to C₆ alkyl)amino, —CHO, a C₁ to C₆ alkylcarbonyl, a C₁ to C₆ haloalkylcarbonyl, a C₁ to C₆ alkoxycarbonyl, a C₁ to C₆ haloalkoxycarbonyl, a C₁ to C₆ alkylaminocarbonyl, a di(C₁ to C₆ alkyl)aminocarbonyl, a phenyl, a phenyl substituted with (Z)_(p1) or D1 to D38, R²⁴ represents a hydrogen atom, a C₁ to C₈ alkyl, a (C₁ to C₈) alkyl optionally substituted with R³⁰, a C₃ to C₈ cycloalkyl, a (C₃ to C₈) cycloalkyl optionally substituted with R³⁰, E2 to E6, E12 to E19, a C₃ to C₈ alkenyl, a (C₃ to C₈) alkenyl optionally substituted with R³⁰, a C₃ to C₈ alkynyl, a (C₃ to C₈) alkynyl optionally substituted with R³⁰, —C(O)R³¹, —C(O)OR³², —C(O)SR³², —C(O)N(R³⁴)R³³, —C(O)C(O)R³², —C(O)C(O)OR³², —C(S)R³¹, —C(S)OR³², —C(S)SR³², —C(S)N(R³⁴)R³³, —S(O)₂R³², S(O)₂N(R³⁴)R³³, —Si(R^(11a))(R^(11b))R¹¹, —P(O)(OR²⁰)₂, —P(S)(OR²⁰)₂, a phenyl, a phenyl substituted with (Z)_(p1), D1, D2, D4 to D6, D8 to D10, D12 to D19, D21, D23, D25, D27 or D30 to D38, R²⁵ represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₁ to C₄ alkoxy(C₁ to C₄) alkyl, a C₁ to C₄ alkylthio(C₁ to C₄) alkyl, a C₃ to C₆ cycloalkyl, a C₃ to C₆ alkenyl, a C₃ to C₆ alkynyl, a C₁ to C₆ alkoxy, a phenyl or a phenyl substituted with (Z)_(p1), or R²⁵ together with R²⁴ optionally forms a C₂ to C₅ alkylene chain to form together with a nitrogen atom to which R²⁴ and R²⁵ are bonded, a 3- to 6-membered ring, and in this case, the alkylene chain optionally contains one oxygen atom, sulfur atom or nitrogen atom and is optionally substituted with a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₆ haloalkyl group, a C₁ to C₆ alkoxy group, a —CHO group, a C₁ to C₆ alkylcarbonyl group, a C₁ to C₆ alkoxycarbonyl group, a phenyl group, a phenyl group substituted with (Z)_(p1), an oxo group or a thioxo group, R²⁶ represents a C₁ to C₈ alkyl, a (C₁ to C₈) alkyl optionally substituted with R³⁰, a C₃ to C₈ cycloalkyl, a (C₃ to C₈) cycloalkyl optionally substituted with R³⁰, E2 to E6, E12 to E19, a C₃ to C₈ alkenyl, a (C₃ to C₈) alkenyl optionally substituted with R³⁰, a C₃ to C₈ alkynyl, a (C₃ to C₈) alkynyl optionally substituted with R³⁰, —C(O)R³¹, —C(O)OR³², —C(O)SR³², —C(O)N(R³⁴)R³³, —C(O)C(O)R³², —C(O)C(O)OR³², —C(S)R³¹, —C(S)OR³², —C(S)SR³², —C(S)N(R³⁴)R³³, —SH, a C₁ to C₆ alkylthio, a C₁ to C₆ haloalkylthio, a phenylthio, a phenylthio substituted with (Z)_(p1), —P(O)(OR²⁰)₂, —P(S)(OR²⁰)₂, a phenyl, a phenyl substituted with (Z)_(p1), D9, D10, D12, D14 to D17, D30, D32 or D34, R²⁷ represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₃ to C₆ cycloalkyl(C₁ to C₄) alkyl, a C₁ to C₆ alkoxy(C₁ to C₄) alkyl, a C₁ to C₆ haloalkoxy(C₁ to C₄) alkyl, a C₁ to C₆ alkylthio(C₁ to C₄) alkyl, a C₁ to C₆ haloalkylthio(C₁ to C₄) alkyl, a C₁ to C₆ alkylsulfonyl(C₁ to C₄) alkyl, a C₁ to C₆ haloalkylsulfonyl(C₁ to C₄) alkyl, a phenyl(C₁ to C₄) alkyl, a phenyl(C₁ to C₄) alkyl substituted with (Z)_(p1), a C₃ to C₆ cycloalkyl, a phenyl or a phenyl substituted with (Z)_(p1), R²⁸ represents a C₁ to C₈ alkyl, a (C₁ to C₈) alkyl optionally substituted with R³⁰, a C₃ to C₈ cycloalkyl, a (C₃ to C₈) cycloalkyl optionally substituted with R³⁰, E1 to E7, E12 to E19, a C₂ to C₈ alkenyl, a (C₂ to C₈) alkenyl optionally substituted with R³⁰, a C₃ to C₈ alkynyl, a (C₃ to C₈) alkynyl optionally substituted with R³⁰, a phenyl, a phenyl substituted with (Z)_(p1), D1 to D25 or D27 to D38, R²⁹ represents a hydrogen atom, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R³⁰, a C₃ to C₆ alkenyl, a C₃ to C₆ haloalkenyl, a C₃ to C₆ alkynyl, a C₃ to C₆ haloalkynyl, a phenyl or a phenyl substituted with (Z)_(p1), or R²⁹ together with R²⁸ optionally forms a C₂ to C₅ alkylene chain to form together with a nitrogen atom to which R²⁸ and R²⁹ are bonded, a 3- to 6-membered ring, and in this case, the alkylene chain optionally contains one oxygen atom, sulfur atom or nitrogen atom and is optionally substituted with a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₆ alkoxy group, a —CHO group, a C₁ to C₆ alkylcarbonyl group, a C₁ to C₆ alkoxycarbonyl group, a phenyl group or a phenyl group substituted with (Z)_(p1), R³⁰ represents a halogen atom, a cyano, a nitro, a C₃ to C₈ cycloalkyl, a C₃ to C₈ halocycloalkyl, E4, E5, E7, E8, E10, E12, E13, E15, E16, E18, a C₂ to C₆ alkenyl, a C₂ to C₆ haloalkenyl, a C₅ to C₈ cycloalkenyl, —OH, —OR³², —OC(O)R³¹, —OC(O)OR³², —OC(O)N(R³⁴)R³³, —OC(S)N(R³⁴)R³³, —SH, —S(O)_(r)R³², —S(═NR³³)R³², —S(R³²)═NC(O)R³¹, —S(O)(═NR³³)R³², —S(O)(R³²)═NC(O)R³¹, —SC(O)R³¹, —SC(O)OR³², —SC(O)N(R³⁴)R³³, —SC(S)N(R³⁴)R³³, —N(R³⁴)R³³, —N(R³⁴)C(O)R³¹, —N(R³⁴)C(O)OR³², —N(R³⁴)C(O)SR³², —N(R³⁴)C(O)N(R³⁴)R³³, —N(R³⁴)C(S)N(R³⁴)R³³, —N(R³⁴)S(O)₂R³², —C(O)R³¹, —C(O)OH, —C(O)OR³², —C(O)SR³², —C(O)N(R³⁴)R³³, —C(O)C(O)OR³², —C(═NOR³²)N(R³⁴)R³³, —C(═NOR³²)NR³⁴)C(O)R³¹, —Si(R^(11a))(R^(11b))R¹¹, —P(O)(OR²⁰)₂, —P(S)(OR²⁰)₂, —P(phenyl)₂, —P(O)(phenyl)₂, a phenyl, a phenyl substituted with (Z)_(p1) or D1 to D38, R³¹ represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a (C₁ to C₄) alkyl optionally substituted with R³⁵, a C₃ to C₆ cycloalkyl, a C₃ to C₆ halocycloalkyl, E4, E5, E12, E13, a C₂ to C₈ alkenyl, a C₂ to C₈ haloalkenyl, a C₅ to C₁₀ cycloalkenyl, a C₅ to C₁₀ halocycloalkenyl, a C₂ to C₈ alkynyl, a C₂ to C₈ haloalkynyl, a phenyl, a phenyl substituted with (Z)_(p1) or D1 to D38, R³² represents a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a (C₁ to C₄) alkyl optionally substituted with R³⁵, a (C₁ to C₄) haloalkyl optionally substituted with R³⁵, a C₃ to C₆ cycloalkyl, E4, E5, a C₂ to C₈ alkenyl, a C₂ to C₈ haloalkenyl, a C₃ to C₈ alkynyl, a C₃ to C₈ haloalkynyl, a phenyl, a phenyl substituted with (Z)_(p1), D12, D32 or D34, R³³ represents a hydrogen atom, a cyano, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a (C₁ to C₄) alkyl optionally substituted with R³⁵, a C₃ to C₆ cycloalkyl, E4, E5, E12, a C₂ to C₈ alkenyl, a C₂ to C₈ haloalkenyl, a C₃ to C₈ alkynyl, a phenyl, a phenyl substituted with (Z)_(p1), D1 to D25 or D27 to D38, R³⁴ represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a cyano(C₁ to C₆) alkyl, a C₃ to C₆ cycloalkyl(C₁ to C₄) alkyl, a C₃ to C₈ cycloalkyl, a C₃ to C₆ alkenyl or a C₃ to C₆ alkynyl, or R³⁴ together with R³³ optionally forms a C₂ to C₅ alkylene chain to form together with a nitrogen atom to which R³³ and R³⁴ are bonded, a 3- to 6-membered ring, and in this case, the alkylene chain optionally contains one oxygen atom, sulfur atom or nitrogen atom and is optionally substituted with a halogen atom, a C₁ to C₄ alkyl group, a C₁ to C₄ alkoxy group, a —CHO group, a C₁ to C₄ alkylcarbonyl group, a C₁ to C₄ alkoxycarbonyl group, a phenyl group or a phenyl group substituted with (Z)_(p1), R³⁵ represents a cyano, a C₃ to C₆ cycloalkyl, a C₃ to C₆ halocycloalkyl, E4, E5, E12, E13, a C₁ to C₄ alkoxy, a C₁ to C₄ haloalkoxy, a phenoxy, a phenoxy substituted with (Z)_(p1), a C₁ to C₄ alkylthio, a C₁ to C₄ haloalkylthio, a phenylthio, a phenylthio substituted with (Z)_(p1), a C₁ to C₄ alkylsulfonyl, a C₁ to C₄ haloalkylsulfonyl, a phenylsulfonyl, a phenylsulfonyl substituted with (Z)_(p1), —N(R³⁷)R³⁶, a C₁ to C₆ alkylcarbonyl, a C₁ to C₆ haloalkylcarbonyl, a C₁ to C₆ alkoxycarbonyl, a C₁ to C₆ alkylaminocarbonyl, a di(C₁ to C₆ alkyl)aminocarbonyl, a tri(C₁ to C₄ alkyl) silyl, a phenyl, a phenyl substituted with (Z)_(p1), a naphthyl or D1 to D38, R³⁶ represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ alkylcarbonyl, a C₁ to C₆ haloalkylcarbonyl, a C₁ to C₆ alkoxycarbonyl, a phenylcarbonyl or a phenylcarbonyl substituted with (Z)_(p1), R³⁷ represents a hydrogen atom or a C₁ to C₆ alkyl, m represents an integer of 0 to 5, n represents an integer of 0 to 4, p represents an integer of 0 to 4, p1 represents an integer of 1 to 5, q represents an integer of 0 to 8, r represents an integer of 0 to 2, and t represents an integer of 0 or 1), and a salt of the substituted isoxazoline compound or a salt of the substituted enone oxime compound.
 2. The substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound according to claim 1, wherein X represents a halogen atom, a cyano, a nitro, —SF₅, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a hydroxy(C₁ to C₄) haloalkyl, a C₁ to C₄ alkoxy(C₁ to C₄) haloalkyl, —OR⁵ or —S(O)_(r)R⁵, where when m represents an integer of 2 or more, Xs are optionally the same as or different from each other, Y represents a halogen atom, a cyano, a nitro, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a (C₁ to C₄) alkyl optionally substituted with R⁴, a C₂ to C₆ alkenyl, a C₂ to C₆ alkynyl, —OR⁵, —S(O)_(r)R⁵, —NH₂, —N(R⁷)R⁶, —C(S)NH₂, D1 to D3, D7, D11 or D22, where when n represents an integer of 2 or more, Ys are optionally the same as or different from each other, Z^(a) represents a halogen atom, a cyano, a nitro, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₁ to C₆ alkoxy, a C₁ to C₆ haloalkoxy, a C₁ to C₆ alkylthio, a C₁ to C₆ haloalkylthio, a C₁ to C₆ alkylsulfinyl, a C₁ to C₆ haloalkylsulfinyl, a C₁ to C₆ alkylsulfonyl, a C₁ to C₆ haloalkylsulfonyl, —NH₂, —C(O)N(R²)R¹ or —C(S)N(R²)R¹, where when p represents an integer of 2 or more, Z^(a)s are optionally the same as or different from each other, R³ represents a C₁ to C₆ haloalkyl or a C₃ to C₈ halocycloalkyl, R^(3a) represents a halogen atom, a C₁ to C₆ alkyl or a C₁ to C₆ alkylthio, R^(3b) represents a hydrogen atom or a halogen atom, R^(3c) represents a hydrogen atom, a halogen atom or a C₁ to C₆ alkyl, R⁴ represents —OH, a C₁ to C₄ alkoxy, a C₁ to C₄ haloalkoxy, a C₁ to C₄ alkylthio, a C₁ to C₄ haloalkylthio, a C₁ to C₄ alkylsulfinyl, a C₁ to C₄ haloalkylsulfinyl, a C₁ to C₄ alkylsulfonyl or a C₁ to C₄ haloalkylsulfonyl, R⁵ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl or a C₁ to C₂ haloalkoxy(C₁ to C₂) haloalkyl, R⁶ represents a C₁ to C₄ alkyl, —C(O)R⁸, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹, —C(S)SR⁹ or —S(O)₂R⁹, R⁷ represents a hydrogen atom or a C₁ to C₄ alkyl, R⁸ represents a hydrogen atom, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl or a C₃ to C₆ cycloalkyl, and R⁹ represents a C₁ to C₄ alkyl or a C₁ to C₄ haloalkyl.
 3. The substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound according to claim 2, wherein A¹ represents a carbon atom or a nitrogen atom, A², A³ and A⁴ individually represent a carbon atom, G¹ represents a benzene ring, G² represents a structure represented by G²-1, G²-2, G²-4, G²-6, G²-7, G²-9 or G²-10, L represents —C(R^(4a))(R^(4b))—, X represents a halogen atom, a cyano, a nitro, —SF₅, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₁ to C₄ alkoxy, a C₁ to C₄ haloalkoxy, a C₁ to C₄ alkylthio or a C₁ to C₄ haloalkylthio, where when m represents 2 or 3, Xs are optionally the same as or different from each other, Y represents a halogen atom, a cyano, a nitro, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₁ to C₂ alkoxy(C₁ to C₂) alkyl, a C₂ to C₄ alkynyl, a C₁ to C₄ alkoxy, a C₁ to C₄ haloalkoxy, a C₁ to C₄ alkylthio, a C₁ to C₄ haloalkylthio, —N(R⁷)R⁶ or —C(S)NH₂, Z^(a) represents a halogen atom, a cyano, a nitro, a C₁ to C₄ alkyl, —NH₂, —C(O)N(R²)R¹ or —C(S)N(R²)R¹, where when p represents an integer of 2 or more, Z^(a)s are optionally the same as or different from each other, R¹ represents a hydrogen atom, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R¹³, a C₃ to C₆ cycloalkyl, a (C₃ to C₆) cycloalkyl optionally substituted with R¹³, E4, E5, E12, a C₃ to C₆ alkenyl, a C₃ to C₆ haloalkenyl, a C₃ to C₆ alkynyl, a C₁ to C₆ alkylcarbonyl, —CH═NOR¹⁵, —C(O)OR¹⁵, —C(O)N(R¹⁷)R¹⁶, —C(S)OR¹⁵, —C(S)N(R¹⁷)R¹⁶, —C(OR¹⁵)═NOR¹⁵, —C(NH₂)═NCN, —C(NH₂)═NOR¹⁵, —C(NH₂)═NNO₂, —N(R¹⁷)R¹⁶, a phenyl substituted with (Z)_(p1), D1, D5 to D8, D10, D17 or D32 to D35, R² represents a hydrogen atom, a C₁ to C₆ alkyl, a (C₁ to C₄) alkyl substituted with R^(13a), a C₃ to C₆ cycloalkyl, a C₃ to C₆ alkenyl, a C₃ to C₆ alkynyl, —C(O)R^(14a), —C(O)OR^(15a), —C(O)C(O)OR^(15a) or a C₁ to C₆ haloalkylthio, or R² together with R¹ optionally forms ═C(R^(2b))R^(1b), R^(1a) represents —C(O)R¹⁴, —C(O)OR¹⁵, —C(O)SR¹⁵, —C(O)N(R¹⁷)R¹⁶, —C(O)N(R¹⁷)N(R¹⁷)R¹⁶ or —C(S)R¹⁴, R^(2a) represents a hydrogen atom, a C₁ to C₆ alkyl, a (C₁ to C₄) alkyl substituted with R^(13a), a C₃ to C₆ alkenyl or a C₃ to C₆ alkynyl, R^(1b) represents a C₁ to C₆ alkyl, a C₁ to C₆ alkoxy, a C₁ to C₆ haloalkoxy, a C₁ to C₆ alkylthio or —N(R^(17b))R^(16b), R^(2b) represents a C₁ to C₆ alkylthio or —N(R^(17c))R^(16c), or R^(2b) together with R^(1b) optionally forms —N(R^(17c))CH═CHS— to form together with a carbon atom to which R^(1b) and R^(2b) are bonded, a 5-membered ring, R³ represents a C₁ to C₄ haloalkyl, R^(3a) represents a halogen atom or a C₁ to C₂ alkyl, R^(3b) represents a hydrogen atom, R^(3c) represents a hydrogen atom, a halogen atom or a C₁ to C₂ alkyl, Z represents a halogen atom, a cyano, a nitro, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₁ to C₄ alkoxy, a C₁ to C₄ alkylsulfonyloxy or a C₁ to C₄ alkylthio, where when p and p1 individually represent an integer of 2 or more, Zs are optionally the same as or different from each other, R^(4a) represents a hydrogen atom, a cyano, a C₁ to C₂ alkyl, a C₁ to C₂ haloalkyl, a C₂ to C₄ alkynyl or —C(S)NH₂, R^(4b) represents a hydrogen atom, R⁶ represents a hydrogen atom, a C₁ to C₄ alkyl, —CHO, a C₁ to C₄ alkylcarbonyl, a C₁ to C₄ haloalkylcarbonyl, a C₁ to C₄ alkoxycarbonyl, a C₁ to C₄ alkylthiocarbonyl, a C₁ to C₄ alkoxythiocarbonyl or a C₁ to C₄ alkyldithiocarbonyl, R⁷ represents a hydrogen atom or a C₁ to C₄ alkyl, R¹² represents a C₁ to C₄ alkyl, R¹³ represents a halogen atom, a cyano, a C₃ to C₄ cycloalkyl, E4, E7, —OR²⁴, —N(R²⁵)R²⁴, —S(O)_(r)R²⁶, a C₁ to C₄ alkylcarbonyl, —C(R²⁷)═NOR²⁸, —C(O)N(R²⁹)R²⁸, —C(S)NH₂, a phenyl, a phenyl substituted with (Z)_(p1), D1, D5, D7, D8, D10, D13, D16, D17, D22, D32 or D34, R^(13a) represents a cyano, a C₃ to C₄ cycloalkyl, —OR²⁴, —S(O)_(r)R²⁶, a C₁ to C₄ alkoxycarbonyl or D32, R¹⁴ represents a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R³⁰, a C₃ to C₆ cycloalkyl, E4, E5, E10, a C₂ to C₆ alkenyl, a C₂ to C₆ haloalkenyl, a C₂ to C₆ alkynyl, a phenyl substituted with (Z)_(p1) or D32, R^(14a) represents a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₁ to C₄ alkoxy(C₁ to C₄) alkyl, a C₁ to C₄ alkylthio(C₁ to C₄) alkyl, a C₁ to C₄ alkylsulfinyl(C₁ to C₄) alkyl, a C₁ to C₄ alkylsulfonyl(C₁ to C₄) alkyl, a C₃ to C₆ cycloalkyl, a C₂ to C₆ alkenyl, a C₂ to C₆ alkynyl, a phenyl, a phenyl substituted with (Z)_(p1) or D32, R¹⁵ represents a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₃ to C₄ cycloalkyl(C₁ to C₄) alkyl, a C₁ to C₄ alkoxycarbonyl(C₁ to C₄) alkyl or a C₃ to C₆ alkenyl, R^(15a) represents a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl, a C₁ to C₄ alkoxy(C₁ to C₄) alkyl, a C₃ to C₆ alkenyl, a C₃ to C₆ alkynyl or a phenyl, R¹⁶ represents a hydrogen atom, a C₁ to C₆ alkyl, a (C₁ to C₆) alkyl optionally substituted with R³⁰, a C₃ to C₆ cycloalkyl, a C₃ to C₆ alkenyl, a C₃ to C₆ alkynyl, a C₁ to C₆ alkylcarbonyl, a C₁ to C₆ haloalkylcarbonyl, a C₁ to C₆ alkoxycarbonyl, a phenyl, a phenyl substituted with (Z)_(p1), D32 or D34, R¹⁷ represents a hydrogen atom, a C₁ to C₆ alkyl, a C₃ to C₆ alkenyl or a C₃ to C₆ alkynyl, or R¹⁷ together with R¹⁶ optionally forms a C₃ to C₅ alkylene chain to form together with a nitrogen atom to which R¹⁶ and R¹⁷ are bonded, a 4- to 6-membered ring, and in this case, the alkylene chain optionally contains one sulfur atom, R^(16b) represents a cyano, a nitro or a C₁ to C₆ alkoxy, R^(17b) represents a hydrogen atom or a C₁ to C₆ alkyl, R^(16c) represents a hydrogen atom, a C₁ to C₆ alkyl, a C₁ to C₆ haloalkyl or a C₁ to C₆ alkoxy, R^(17c) represents a hydrogen atom or a C₁ to C₆ alkyl, R²¹ represents a C₁ to C₂ alkyl, R²⁴ represents a hydrogen atom, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, —C(O)R³¹ or —C(O)OR³², R²⁵ represents a hydrogen atom or a C₁ to C₄ haloalkyl, R²⁶ represents a C₁ to C₄ alkyl, R²⁷ represents a hydrogen atom or a C₁ to C₄ alkyl, R²⁸ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a hydroxy(C₁ to C₄) haloalkyl, a C₃ to C₄ cycloalkyl, a C₃ to C₄ alkenyl or a C₃ to C₄ alkynyl, R²⁹ represents a hydrogen atom or a C₁ to C₄ alkyl, R³⁰ represents a halogen atom, a C₃ to C₆ cycloalkyl, a C₁ to C₄ alkoxy, a C₁ to C₄ haloalkoxy, —S(O)_(r)R³², —S(R³²)═NC(O)R³¹, —S(O)(R³²)═NH, —N(R³⁴)R³³, —N(R³⁴)C(O)R³¹, —N(R³⁴)C(O)OR³², —C(O)N(R³⁴)R³³, a phenyl substituted with (Z)_(p1) or D32, R³¹ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl or a C₃ to C₆ cycloalkyl, R³² represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl or a cyano(C₁ to C₂) alkyl, R³³ represents a hydrogen atom, a C₁ to C₄ alkyl or a cyano(C₁ to C₂) alkyl, R³⁴ represents a hydrogen atom or a cyano(C₁ to C₂) alkyl, m represents an integer of 1 to 3, n represents an integer of 0 or 1, p represents an integer of 0 to 2, p1 represents an integer of 1 to 3, q represents an integer of 0 or 1, and t represents
 0. 4. The substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound according to claim 3, wherein G² represents a structure represented by G²-1, G²-2, G²-7 or G²-10, X represents a halogen atom, a cyano, —SF₅, a C₁ to C₂ haloalkyl, a C₁ to C₂ haloalkoxy or a C₁ to C₂ haloalkylthio, where when m represents 2 or 3, Xs are optionally the same as or different from each other, Y represents a halogen atom, a cyano, a nitro, a C₁ to C₂ alkyl, a C₁ to C₂ haloalkyl, a C₁ to C₂ alkoxymethyl, a C₂ to C₃ alkynyl, a C₁ to C₂ haloalkoxy, a C₁ to C₂ haloalkylthio, —N(R⁷)R⁶ or —C(S)NH₂, Z^(a) represents a halogen atom, a nitro, a methyl or —NH₂, R¹ represents a C₁ to C₄ alkyl, a (C₁ to C₄) alkyl optionally substituted with R¹³, a C₃ to C₄ cycloalkyl, a cyclopropyl substituted with R¹³, E4, E5, a C₃ to C₄ alkenyl, a C₃ to C₄ haloalkenyl, —CH═NOR¹⁵, —C(O)OR¹⁵, —C(O)NHR¹⁶, —C(S)OR¹⁵, —N(R¹⁷)R¹⁶, D34 or D35, R² represents a hydrogen atom, a C₁ to C₄ alkyl, a (C₁ to C₂) alkyl substituted with R^(13a), a C₃ to C₄ alkynyl, —C(O)R^(14a), —C(O)OR^(15a) or a C₁ to C₄ haloalkylthio, or R² together with R¹ optionally forms ═C(R^(2b))R^(1b), R^(1a) represents —C(O)R¹⁴, —C(O)N(R¹⁷)R¹⁶ or —C(S)R¹⁴, R^(2a) represents a hydrogen atom, a C₁ to C₄ alkyl, a (C₁ to C₂) alkyl substituted with R^(13a), a C₃ to C₄ alkenyl or a C₃ to C₄ alkynyl, R^(1b) represents a C₁ to C₄ alkoxy or a C₁ to C₄ alkylthio, R^(2b) represents —NHR^(16c), R³ represents a C₁ to C₂ haloalkyl, R^(3a) represents a halogen atom or a methyl, R^(3c) represents a hydrogen atom, Z represents a halogen atom, a cyano or a nitro, R^(4a) represents a hydrogen atom, a cyano, a methyl or —C(S)NH₂, R⁶ represents a hydrogen atom, a C₁ to C₂ alkyl or a C₁ to C₂ alkylcarbonyl, R⁷ represents a hydrogen atom or a C₁ to C₂ alkyl, R¹³ represents a halogen atom, a cyano, a C₃ to C₄ cycloalkyl, E4, E7, —OR²⁴, —NHR²⁴, —C(R²⁷)═NOR²⁸, —C(O)N(R²⁹)R²⁸, a phenyl, a phenyl substituted with (Z)_(p1), D8, D10, D13, D16, D22, D32 or D34, R¹² represents a methyl, R^(13a) represents a cyano, a C₃ to C₄ cycloalkyl, —OR²⁴ or a C₁ to C₄ alkylthio, R¹⁴ represents a C₁ to C₄ alkyl, a (C₁ to C₄) alkyl optionally substituted with R³⁰, a C₃ to C₄ cycloalkyl, E4, E5, a C₂ to C₄ alkenyl, a C₂ to C₄ alkynyl or a phenyl substituted with (Z)_(p1), R^(14a) represents a C₁ to C₄ alkyl, a C₁ to C₂ alkoxy(C₁ to C₂) alkyl, a C₃ to C₄ cycloalkyl or a C₂ to C₄ alkenyl, R¹⁵ represents a C₁ to C₄ alkyl, R^(15a) represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl or a C₁ to C₂ alkoxy(C₁ to C₂) alkyl, R¹⁶ represents a hydrogen atom, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₃ to C₄ cycloalkyl, a C₃ to C₄ alkynyl, a phenyl, D32 or D34, R¹⁷ represents a hydrogen atom, a C₁ to C₄ alkyl, a C₃ to C₄ alkenyl or a C₃ to C₄ alkynyl, R^(16c) represents a hydrogen atom or a C₁ to C₄ alkyl, R²¹ represents a methyl, R²⁴ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₁ to C₄ alkylcarbonyl or a C₁ to C₄ alkoxycarbonyl, R²⁷ represents a hydrogen atom or a C₁ to C₂ alkyl, R²⁸ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₃ to C₄ alkenyl or a C₃ to C₄ alkynyl, R²⁹ represents a hydrogen atom or a C₁ to C₂ alkyl, R³⁰ represents a halogen atom, a C₃ to C₄ cycloalkyl, —S(O)_(r)R³², —N(R³⁴)R³³ or —C(O)N(R³⁴)R³³, R³² represents a C₁ to C₄ alkyl or a C₁ to C₄ haloalkyl, R³³ represents a C₁ to C₄ alkyl or a cyano(C₁ to C₂) alkyl, and R³⁴ represents a hydrogen atom.
 5. The substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound according to claim 4, wherein A¹ represents a carbon atom, G² represents a structure represented by G²-1, W represents an oxygen atom, X represents a halogen atom or a trifluoromethyl, where when m represents 2 or 3, Xs are optionally the same as or different from each other, Y represents a halogen atom, a methyl, an ethyl or a trifluoromethyl, R¹ represents a (C₁ to C₂) alkyl substituted with R¹³, E4, —CH═NOR¹⁵, —C(O)OR¹⁵, —C(O)NH₂, —N(R¹⁷)R¹⁶, D34 or D35, R² represents a hydrogen atom, a (C₁ to C₂) alkyl substituted with R^(13a), a C₁ to C₃ alkylcarbonyl, a cyclopropylcarbonyl or a C₁ to C₃ alkoxycarbonyl, R³ represents a trifluoromethyl or a chlorodifluoromethyl, Z represents a halogen atom or a cyano, R¹³ represents a halogen atom, a C₁ to C₃ alkoxy, a C₁ to C₂ haloalkoxy, —C(O)NHR²⁸, D10 or D32, R^(13a) represents —OR²⁴, R¹⁵ represents a C₁ to C₂ alkyl, R¹⁶ represents a phenyl or D34, R¹⁷ represents a C₁ to C₂ alkyl, R²⁴ represents a C₁ to C₂ alkyl or a C₁ to C₂ alkylcarbonyl, R²⁸ represents a C₁ to C₂ haloalkyl, p represents an integer of 0 or 1, and q represents
 0. 6. The substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound according to claim 4, wherein A¹ represents a carbon atom, G² represents a structure represented by G²-2, X represents a halogen atom or a trifluoromethyl, where when m represents 2 or 3, Xs are optionally the same as or different from each other, Y represents a halogen atom, a nitro or a methyl, R^(1a) represents —C(O)R¹⁴ or —C(O)NHR¹⁶, R^(2a) represents a hydrogen atom, a C₁ to C₂ alkyl, a (C₁ to C₂) alkyl substituted with R^(13a) or a propargyl, R³ represents a trifluoromethyl or a chlorodifluoromethyl, R^(4a) represents a hydrogen atom, a cyano or a methyl, R^(13a) represents a cyano, a cyclopropyl or a C₁ to C₂ alkoxy, R¹⁴ represents a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a (C₁ to C₂) alkyl substituted with R³⁰, a C₃ to C₄ cycloalkyl or E4, R¹⁶ represents a C₁ to C₂ alkyl, a cyclopropyl or a propargyl, R³⁰ represents a cyclopropyl, a C₁ to C₂ alkylthio, a C₁ to C₂ alkylsulfinyl or a C₁ to C₂ alkylsulfonyl, and q represents
 0. 7. The substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound according to claim 4, wherein A¹ represents a carbon atom, G² represents a structure represented by G²-7 or G²-10, X represents a halogen atom or a trifluoromethyl, where when m represents 2 or 3, Xs are optionally the same as or different from each other, Y represents a cyano or a nitro, R³ represents a trifluoromethyl or a chlorodifluoromethyl, and p represents
 0. 8. A substituted isoxazoline compound or a substituted enone oxime compound represented by General Formula (3) or General Formula (4):

(where A¹ and A² independently represent a carbon atom or a nitrogen atom, Q represents a halogen atom, a cyano, a nitro, —CH(R^(4a))—R^(a), —OH, a C₁ to C₄ alkoxy, a C₁ to C₄ haloalkoxy, a halosulfonyloxy, a C₁ to C₄ alkylsulfonyloxy, a C₁ to C₄ haloalkylsulfonyloxy, a phenylsulfonyloxy, a phenylsulfonyloxy substituted with (Z)_(p1), a C₁ to C₄ alkylthio, a C₁ to C₄ alkylsulfinyl, a C₁ to C₄ alkylsulfonyl, a C₁ to C₄ haloalkylthio, a C₁ to C₄ haloalkylsulfinyl, a C₁ to C₄ haloalkylsulfonyl, —NH₂ or —C(O)R^(b), X¹ represents a halogen atom, —SF₅, a C₁ to C₄ haloalkyl, a C₁ to C₄ haloalkoxy or a C₁ to C₄ haloalkylthio, X² represents a halogen atom, a cyano, a nitro, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₁ to C₄ alkoxy, a C₁ to C₄ haloalkoxy, a C₁ to C₄ alkylthio or a C₁ to C₄ haloalkylthio, where when m1 represents 2, X²s are optionally the same as or different from each other, Y represents a halogen atom, a cyano, a nitro, a C₁ to C₄ alkyl, a C₁ to C₄ haloalkyl, a C₁ to C₂ alkoxy(C₁ to C₂) alkyl, a C₂ to C₄ alkynyl, a C₁ to C₄ alkoxy, a C₁ to C₄ haloalkoxy, a C₁ to C₄ alkylthio, a C₁ to C₄ haloalkylthio, —N(R⁷)R⁶ or —C(S)NH₂, Z represents a halogen atom or a methyl, where when p1 represents an integer of 2 or more, Zs are optionally the same as or different from each other, R^(a) represents a hydrogen atom, a halogen atom, —OH, a C₁ to C₂ alkylcarbonyloxy, a C₁ to C₂ alkylsulfonyloxy, a C₁ to C₂ haloalkylsulfonyloxy or —NH₂, R^(b) represents a hydrogen atom, a halogen atom, a C₁ to C₂ alkyl, a C₁ to C₂ haloalkyl, —OH, a C₁ to C₄ alkoxy, a 1-pyrazolyl, a 1-imidazolyl or a 1-triazolyl, R³ represents a C₁ to C₄ haloalkyl, R^(3a) represents a halogen atom or a C₁ to C₂ alkyl, R^(3c) represents a hydrogen atom, a halogen atom or a C₁ to C₂ alkyl, R^(4a) represents a hydrogen atom, a C₁ to C₂ alkyl or a C₁ to C₂ haloalkyl, R⁶ represents a hydrogen atom, a C₁ to C₄ alkyl, —CHO, a C₁ to C₄ alkylcarbonyl, a C₁ to a C₄ haloalkylcarbonyl, a C₁ to C₄ alkoxycarbonyl, a C₁ to C₄ alkylthiocarbonyl, a C₁ to C₄ alkoxythiocarbonyl or a C₁ to C₄ alkyldithiocarbonyl, R⁷ represents a hydrogen atom or a C₁ to C₄ alkyl, m1 represents an integer of 0 to 2, n represents an integer of 0 or 1, and p1 represents an integer of 1 to 5), and a salt of the substituted isoxazoline compound or a salt of the substituted enone oxime compound.
 9. The substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound according to claim 8, wherein Q represents a halogen atom, a cyano, a nitro, a C₁ to C₂ alkyl, a C₁ to C₂ haloalkyl, a hydroxy(C₁ to C₂) alkyl, —OH, a C₁ to C₂ alkoxy, a C₁ to C₂ haloalkoxy, a C₁ to C₂ alkylsulfonyloxy, a C₁ to C₂ haloalkylsulfonyloxy, a C₁ to C₂ alkylthio, a C₁ to C₂ alkylsulfinyl, a C₁ to C₂ alkylsulfonyl, —NH₂ or —C(O)R^(b), X¹ represents a halogen atom, —SF₅, a C₁ to C₂ haloalkyl, a C₁ to C₂ haloalkoxy or a C₁ to C₂ haloalkylthio, X² represents a halogen atom, a cyano, a C₁ to C₂ haloalkyl, a C₁ to C₂ haloalkoxy or a C₁ to C₂ haloalkylthio, where when m1 represents 2, X²s are optionally the same as or different from each other, Y represents a halogen atom, a cyano, a nitro, a C₁ to C₂ alkyl, a C₁ to C₂ haloalkyl, a C₁ to C₂ alkoxymethyl, a C₂ to C₃ alkynyl, a C₁ to C₂ haloalkoxy, a C₁ to C₂ haloalkylthio, —N(R⁷)R⁶ or —C(S)NH₂, R^(b) represents a hydrogen atom, a halogen atom, a methyl, —OH or a C₁ to C₂ alkoxy, R³ represents a C₁ to C₂ haloalkyl, R^(3a) represents a halogen atom or a methyl, R⁶ represents a hydrogen atom, a C₁ to C₂ alkyl or a C₁ to C₂ alkylcarbonyl, and R⁷ represents a hydrogen atom or a C₁ to C₂ alkyl.
 10. The substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound according to claim 9, wherein A¹ represents a carbon atom or a nitrogen atom, A² represents a carbon atom, Q represents a halogen atom, a cyano, a nitro, a methylthio, a methylsulfinyl or a methylsulfonyl, X¹ and X² independently represent a halogen atom or a trifluoromethyl, where when m1 represents 2, X²s are optionally the same as or different from each other, Y represents a halogen atom, a cyano, a nitro, a methyl, an ethyl or a trifluoromethyl, R³ represents a trifluoromethyl or a chlorodifluoromethyl, and R^(3a) represents a halogen atom or a methyl.
 11. A pest control agent containing one type or two or more types selected from the substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound as claimed in claim 1, as active ingredient(s).
 12. An agricultural chemical containing one type or two or more types selected from the substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound as claimed in claim 1, as active ingredient(s).
 13. A control agent against internal or external parasites of mammals or birds containing one type or two or more types selected from the substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound as claimed in claim 1, as active ingredient(s).
 14. An insecticide or a miticide containing one type or two or more types selected from the substituted isoxazoline compound or the substituted enone oxime compound and the salt of the substituted isoxazoline compound or the salt of the substituted enone oxime compound as claimed in claim 1, as active ingredient(s). 